Download citation
Download citation
link to html
The Cu atom in the title compound, [Cu(C17H14N3O)2]·2C5H5N, is chelated by the deprotonated Schiff base in a square-planar geometry; the amine group of the Schiff base forms a hydrogen bond with a pyridine solvent mol­ecule. The Cu atom lies on a center of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037202/bt2181sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037202/bt2181Isup2.hkl
Contains datablock I

CCDC reference: 624006

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.105
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.73 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C5 H5 N
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 0 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

Computing details top

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis(2-methyl-1H-indole-3-carbaldehyde benzoylhydrazonato-κ2N,O)copper(II) pyridine disolvate top
Crystal data top
[Cu(C17H14N3O)2]·2C5H5NF(000) = 1612
Mr = 774.36Dx = 1.338 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4184 reflections
a = 22.552 (2) Åθ = 2.4–23.8°
b = 9.076 (1) ŵ = 0.62 mm1
c = 19.107 (2) ÅT = 293 K
β = 100.503 (1)°Fragment, brown
V = 3845.5 (5) Å30.36 × 0.23 × 0.17 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
3943 independent reflections
Radiation source: fine-focus sealed tube3103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2828
Tmin = 0.783, Tmax = 0.902k = 1111
16507 measured reflectionsl = 2323
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0541P)2 + 1.8992P]
where P = (Fo2 + 2Fc2)/3
3943 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.25000.75000.50000.0434 (1)
O10.3092 (1)0.8700 (2)0.5580 (1)0.0493 (4)
N10.2275 (1)0.9414 (2)0.6078 (1)0.0445 (4)
N20.1973 (1)0.8448 (2)0.5564 (1)0.0427 (4)
N30.0015 (1)0.9523 (2)0.5997 (1)0.0508 (4)
N40.1254 (1)0.9620 (3)0.6111 (1)0.0696 (6)
C10.3258 (1)1.0368 (2)0.6554 (1)0.0431 (5)
C20.3865 (1)1.0467 (2)0.6511 (1)0.0497 (5)
C30.4244 (1)1.1372 (3)0.6971 (1)0.0602 (6)
C40.4028 (1)1.2182 (3)0.7478 (1)0.0598 (6)
C50.3427 (1)1.2088 (3)0.7530 (1)0.0625 (6)
C60.3045 (1)1.1189 (3)0.7070 (1)0.0569 (6)
C70.2851 (1)0.9432 (2)0.6039 (1)0.0426 (5)
C80.1390 (1)0.8354 (2)0.5468 (1)0.0410 (4)
C90.0941 (1)0.9144 (2)0.5764 (1)0.0387 (4)
C100.0360 (1)0.8574 (2)0.5700 (1)0.0422 (4)
C110.0106 (1)0.7152 (3)0.5393 (1)0.0585 (6)
C120.0345 (1)1.0751 (2)0.6243 (1)0.0494 (5)
C130.0159 (1)1.2013 (3)0.6555 (1)0.0674 (7)
C140.0569 (1)1.3105 (3)0.6737 (2)0.0792 (8)
C150.1156 (1)1.2972 (3)0.6609 (2)0.0771 (8)
C160.1339 (1)1.1724 (3)0.6294 (1)0.0602 (6)
C170.0937 (1)1.0568 (2)0.6111 (1)0.0442 (5)
C180.1694 (1)0.8940 (3)0.5690 (2)0.079 (1)
C190.2299 (1)0.9151 (4)0.5733 (2)0.101 (1)
C200.2438 (2)1.0103 (5)0.6227 (3)0.115 (2)
C210.1992 (2)1.0812 (4)0.6653 (2)0.112 (1)
C220.1408 (1)1.0528 (4)0.6591 (2)0.089 (1)
H3n0.036 (1)0.942 (3)0.602 (1)0.077 (8)*
H20.40170.99210.61710.060*
H30.46491.14350.69370.072*
H40.42871.27920.77850.072*
H50.32791.26280.78740.075*
H60.26401.11310.71050.068*
H80.12300.76320.51420.049*
H11a0.02610.69400.49680.088*
H11b0.03260.72230.52790.088*
H11c0.02180.63770.57330.088*
H130.02341.21050.66360.081*
H140.04571.39560.69510.095*
H150.14291.37360.67380.093*
H160.17301.16580.62040.072*
H180.16000.82910.53500.094*
H190.26010.86500.54290.121*
H200.28381.02600.62680.138*
H210.20781.14870.69870.134*
H220.11021.09980.69040.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0317 (2)0.0519 (2)0.0490 (2)0.0007 (2)0.0136 (1)0.0123 (2)
O10.034 (1)0.061 (1)0.056 (1)0.003 (1)0.015 (1)0.018 (1)
N10.033 (1)0.055 (1)0.046 (1)0.000 (1)0.010 (1)0.012 (1)
N20.033 (1)0.051 (1)0.045 (1)0.001 (1)0.011 (1)0.009 (1)
N30.033 (1)0.065 (1)0.057 (1)0.004 (1)0.016 (1)0.001 (1)
N40.050 (1)0.085 (2)0.079 (2)0.013 (1)0.025 (1)0.015 (1)
C10.039 (1)0.049 (1)0.041 (1)0.001 (1)0.005 (1)0.002 (1)
C20.037 (1)0.061 (1)0.051 (1)0.002 (1)0.005 (1)0.008 (1)
C30.041 (1)0.078 (2)0.058 (1)0.006 (1)0.000 (1)0.005 (1)
C40.056 (1)0.068 (2)0.050 (1)0.009 (1)0.005 (1)0.009 (1)
C50.065 (2)0.074 (2)0.048 (1)0.000 (1)0.008 (1)0.018 (1)
C60.046 (1)0.076 (2)0.049 (1)0.003 (1)0.012 (1)0.016 (1)
C70.036 (1)0.049 (1)0.044 (1)0.001 (1)0.010 (1)0.004 (1)
C80.035 (1)0.047 (1)0.043 (1)0.002 (1)0.011 (1)0.004 (1)
C90.033 (1)0.047 (1)0.038 (1)0.001 (1)0.009 (1)0.000 (1)
C100.035 (1)0.052 (1)0.041 (1)0.004 (1)0.009 (1)0.001 (1)
C110.041 (1)0.071 (2)0.064 (2)0.009 (1)0.012 (1)0.009 (1)
C120.044 (1)0.056 (1)0.052 (1)0.006 (1)0.018 (1)0.001 (1)
C130.061 (2)0.065 (2)0.083 (2)0.010 (1)0.034 (1)0.011 (1)
C140.092 (2)0.061 (2)0.094 (2)0.009 (2)0.041 (2)0.021 (2)
C150.078 (2)0.059 (2)0.101 (2)0.012 (1)0.032 (2)0.025 (2)
C160.053 (1)0.057 (1)0.074 (2)0.003 (1)0.022 (1)0.011 (1)
C170.040 (1)0.050 (1)0.045 (1)0.003 (1)0.013 (1)0.002 (1)
C180.069 (2)0.084 (2)0.086 (2)0.004 (2)0.022 (2)0.0186 (2)
C190.060 (2)0.108 (3)0.131 (3)0.009 (2)0.007 (2)0.047 (2)
C200.070 (2)0.097 (3)0.196 (4)0.025 (2)0.074 (3)0.064 (3)
C210.108 (3)0.091 (2)0.163 (4)0.014 (2)0.096 (3)0.024 (2)
C220.078 (2)0.099 (2)0.099 (2)0.002 (2)0.043 (2)0.007 (2)
Geometric parameters (Å, º) top
Cu1—O11.913 (1)C14—C151.395 (4)
Cu1—O1i1.913 (1)C15—C161.380 (3)
Cu1—N21.944 (2)C16—C171.390 (3)
Cu1—N2i1.944 (2)C18—C191.393 (4)
O1—C71.296 (2)C19—C201.358 (5)
N1—C71.316 (2)C20—C211.338 (6)
N1—N21.398 (2)C21—C221.368 (4)
N2—C81.298 (2)N3—H3n0.85 (1)
N3—C101.354 (3)C2—H20.93
N3—C121.375 (3)C3—H30.93
N4—C181.313 (4)C4—H40.93
N4—C221.327 (4)C5—H50.93
C1—C61.389 (3)C6—H60.93
C1—C21.390 (3)C8—H80.93
C1—C71.483 (3)C11—H11a0.96
C2—C31.379 (3)C11—H11b0.96
C3—C41.374 (3)C11—H11c0.96
C4—C51.381 (4)C13—H130.93
C5—C61.380 (3)C14—H140.93
C8—C91.438 (2)C15—H150.93
C9—C101.393 (3)C16—H160.93
C9—C171.453 (3)C18—H180.93
C10—C111.488 (3)C19—H190.93
C12—C131.390 (3)C20—H200.93
C12—C171.412 (3)C21—H210.93
C13—C141.357 (4)C22—H220.93
O1—Cu1—O1i180C20—C19—C18118.8 (4)
O1—Cu1—N281.96 (6)C21—C20—C19119.0 (3)
O1—Cu1—N2i98.04 (6)C20—C21—C22119.1 (4)
O1i—Cu1—N298.04 (6)N4—C22—C21123.7 (4)
O1i—Cu1—N2i81.96 (6)C10—N3—H3n127 (2)
N2—Cu1—N2i180C12—N3—H3n123 (2)
C7—O1—Cu1110.4 (1)C3—C2—H2119.9
C7—N1—N2109.1 (2)C1—C2—H2119.9
C8—N2—N1119.5 (2)C4—C3—H3119.7
C8—N2—Cu1126.8 (1)C2—C3—H3119.7
N1—N2—Cu1113.5 (1)C3—C4—H4120.1
C10—N3—C12110.0 (2)C5—C4—H4120.1
C18—N4—C22116.8 (2)C6—C5—H5120.1
C6—C1—C2118.55 (19)C4—C5—H5120.1
C6—C1—C7121.78 (18)C5—C6—H6119.5
C2—C1—C7119.65 (18)C1—C6—H6119.5
C3—C2—C1120.3 (2)N2—C8—H8113.6
C4—C3—C2120.6 (2)C9—C8—H8113.6
C3—C4—C5119.8 (2)C10—C11—H11a109.5
C6—C5—C4119.8 (2)C10—C11—H11b109.5
C5—C6—C1120.9 (2)H11a—C11—H11b109.5
O1—C7—N1124.9 (2)C10—C11—H11c109.5
O1—C7—C1117.2 (2)H11a—C11—H11c109.5
N1—C7—C1117.8 (2)H11b—C11—H11c109.5
N2—C8—C9132.9 (2)C14—C13—H13121.1
C10—C9—C8119.9 (2)C12—C13—H13121.1
C10—C9—C17106.7 (2)C13—C14—H14119.5
C8—C9—C17133.3 (2)C15—C14—H14119.5
N3—C10—C9109.3 (2)C16—C15—H15119.4
N3—C10—C11120.5 (2)C14—C15—H15119.4
C9—C10—C11130.2 (2)C15—C16—H16120.2
N3—C12—C13128.8 (2)C17—C16—H16120.2
N3—C12—C17108.3 (2)N4—C18—H18118.7
C13—C12—C17122.8 (2)C19—C18—H18118.7
C14—C13—C12117.9 (2)C20—C19—H19120.6
C13—C14—C15121.0 (2)C18—C19—H19120.6
C16—C15—C14121.1 (3)C21—C20—H20120.5
C15—C16—C17119.7 (2)C19—C20—H20120.5
C16—C17—C12117.5 (2)C20—C21—H21120.5
C16—C17—C9136.7 (2)C22—C21—H21120.5
C12—C17—C9105.7 (2)N4—C22—H22118.1
N4—C18—C19122.6 (3)C21—C22—H22118.1
C7—O1—Cu1—N2i177.6 (1)C12—N3—C10—C11180.0 (2)
C7—O1—Cu1—N22.4 (1)C8—C9—C10—N3178.1 (2)
C7—N1—N2—C8174.2 (2)C17—C9—C10—N31.7 (2)
C7—N1—N2—Cu10.4 (2)C8—C9—C10—C114.1 (3)
O1—Cu1—N2—C8172.5 (2)C17—C9—C10—C11179.5 (2)
O1i—Cu1—N2—C87.5 (2)C10—N3—C12—C13177.0 (2)
O1—Cu1—N2—N11.6 (1)C10—N3—C12—C171.3 (2)
O1i—Cu1—N2—N1178.4 (1)N3—C12—C13—C14178.1 (3)
C6—C1—C2—C30.4 (3)C17—C12—C13—C140.1 (4)
C7—C1—C2—C3177.8 (2)C12—C13—C14—C150.7 (5)
C1—C2—C3—C40.3 (4)C13—C14—C15—C160.1 (5)
C2—C3—C4—C50.1 (4)C14—C15—C16—C171.1 (5)
C3—C4—C5—C60.4 (4)C15—C16—C17—C121.6 (4)
C4—C5—C6—C10.3 (4)C15—C16—C17—C9177.6 (3)
C2—C1—C6—C50.2 (4)N3—C12—C17—C16177.3 (2)
C7—C1—C6—C5178.0 (2)C13—C12—C17—C161.1 (3)
Cu1—O1—C7—N13.2 (3)N3—C12—C17—C90.2 (2)
Cu1—O1—C7—C1177.2 (1)C13—C12—C17—C9178.2 (2)
N2—N1—C7—O11.9 (3)C10—C9—C17—C16175.4 (3)
N2—N1—C7—C1178.6 (2)C8—C9—C17—C160.3 (4)
C6—C1—C7—O1179.6 (2)C10—C9—C17—C120.9 (2)
C2—C1—C7—O12.3 (3)C8—C9—C17—C12176.6 (2)
C6—C1—C7—N10.8 (3)C22—N4—C18—C190.4 (4)
C2—C1—C7—N1177.3 (2)N4—C18—C19—C200.3 (5)
N1—N2—C8—C94.7 (3)C18—C19—C20—C210.3 (5)
Cu1—N2—C8—C9169.2 (2)C19—C20—C21—C221.7 (5)
N2—C8—C9—C10163.9 (2)C18—N4—C22—C211.9 (5)
N2—C8—C9—C1720.8 (4)C20—C21—C22—N42.6 (5)
C12—N3—C10—C91.9 (2)
Symmetry code: (i) x+1/2, y+3/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3n···N40.85 (1)2.07 (1)2.910 (3)169 (3)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds