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In the title compound, [Cu(C22H24N6O2)], the copper(II) ion is coordinated by five N atoms from the chelating macrocyclic ligand, forming a distorted square-pyramidal geometry. The complexes associate as dimers, disposed about a centre of symmetry, linked through weak intermolecular Cu...O coordination and N—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011973/hg6037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011973/hg6037Isup2.hkl
Contains datablock I

CCDC reference: 242280

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.138
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.650 0.802 Tmin' and Tmax expected: 0.745 0.802 RR' = 0.873 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.56 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

[3,6,9,12,23-Pentaazatetracyclo[22.4.0.02,6.014,19]octacosa- 1(28),12,14,16,18,24,26-heptaene-21,22-dione(2-)- κ5N6,N9,N12,N20,N23]copper(II) top
Crystal data top
[Cu(C22H24N6O2)]F(000) = 972
Mr = 468.01Dx = 1.523 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 755 reflections
a = 13.178 (7) Åθ = 2.5–23.1°
b = 11.587 (6) ŵ = 1.10 mm1
c = 14.516 (7) ÅT = 293 K
β = 112.949 (8)°Block, green
V = 2041.0 (18) Å30.26 × 0.24 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4174 independent reflections
Radiation source: fine-focus sealed tube2632 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1016
Tmin = 0.650, Tmax = 0.802k = 1314
11388 measured reflectionsl = 1816
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0669P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
4174 reflectionsΔρmax = 0.60 e Å3
281 parametersΔρmin = 0.57 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0131 (10)
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
Cu10.42186 (4)0.17408 (5)0.36350 (3)0.0294 (2)
N10.3908 (3)0.2070 (3)0.4848 (2)0.0279 (8)
N20.5712 (3)0.1472 (3)0.4628 (2)0.0288 (8)
N30.4982 (3)0.3030 (3)0.2797 (2)0.0322 (8)
N50.4247 (3)0.0713 (3)0.2435 (2)0.0292 (8)
H50.45120.00080.26920.035*
N60.2670 (3)0.1939 (3)0.2766 (2)0.0294 (8)
N40.5996 (3)0.4019 (4)0.4246 (3)0.0527 (11)
H4A0.64190.40500.48710.063*
O10.4624 (2)0.1405 (3)0.6496 (2)0.0385 (8)
O20.6506 (2)0.0813 (3)0.6268 (2)0.0399 (8)
C10.4667 (3)0.1574 (3)0.5669 (3)0.0271 (9)
C20.5737 (3)0.1209 (4)0.5534 (3)0.0287 (9)
C30.6688 (3)0.1400 (4)0.4429 (3)0.0317 (10)
C40.7420 (3)0.0474 (4)0.4748 (3)0.0387 (11)
H40.72950.01100.51310.046*
C50.8331 (4)0.0420 (5)0.4500 (4)0.0551 (14)
H5A0.88040.02100.47010.066*
C60.8542 (4)0.1293 (5)0.3959 (4)0.0605 (16)
H60.91600.12600.37990.073*
C70.7834 (4)0.2216 (5)0.3654 (4)0.0522 (14)
H70.79870.28090.32970.063*
C80.6894 (3)0.2287 (4)0.3866 (3)0.0371 (11)
C90.6140 (3)0.3315 (4)0.3484 (3)0.0405 (11)
H90.64550.38070.31130.049*
C100.4971 (4)0.4673 (4)0.3729 (4)0.0532 (13)
H10A0.51290.54890.37130.064*
H10B0.44710.45750.40670.064*
C110.4466 (4)0.4181 (4)0.2666 (3)0.0431 (12)
H11A0.36700.41230.24320.052*
H11B0.46540.46480.22010.052*
C120.4894 (4)0.2478 (4)0.1861 (3)0.0417 (12)
H12A0.54770.27620.16700.050*
H12B0.41940.26820.13340.050*
C130.4979 (4)0.1171 (4)0.1967 (3)0.0391 (11)
H13A0.47820.08250.13120.047*
H13B0.57340.09590.23720.047*
C140.3085 (3)0.0550 (4)0.1735 (3)0.0340 (10)
H14A0.27760.01140.19400.041*
H14B0.30550.04040.10670.041*
C150.2415 (3)0.1608 (4)0.1723 (3)0.0329 (10)
H15A0.26020.22320.13720.039*
H15B0.16350.14420.13850.039*
C160.1885 (3)0.2250 (4)0.3012 (3)0.0304 (10)
H160.11820.22460.25080.037*
C170.1973 (3)0.2613 (4)0.4000 (3)0.0302 (10)
C180.1001 (4)0.3081 (4)0.4035 (3)0.0399 (11)
H180.03630.30990.34540.048*
C190.0974 (4)0.3510 (4)0.4902 (4)0.0475 (13)
H190.03280.38170.49140.057*
C200.1928 (4)0.3478 (4)0.5763 (4)0.0496 (13)
H200.19220.37830.63540.060*
C210.2886 (4)0.3002 (4)0.5762 (3)0.0407 (11)
H210.35110.29790.63540.049*
C220.2936 (3)0.2551 (3)0.4882 (3)0.0300 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0237 (3)0.0419 (3)0.0213 (3)0.0024 (2)0.0073 (2)0.0005 (2)
N10.0225 (18)0.036 (2)0.0238 (18)0.0000 (15)0.0073 (14)0.0022 (14)
N20.0212 (18)0.036 (2)0.0265 (18)0.0016 (14)0.0063 (14)0.0007 (15)
N30.0301 (19)0.037 (2)0.0279 (19)0.0009 (15)0.0092 (15)0.0030 (15)
N50.0317 (19)0.034 (2)0.0210 (17)0.0036 (15)0.0087 (15)0.0051 (15)
N60.0266 (19)0.037 (2)0.0216 (17)0.0024 (15)0.0058 (14)0.0024 (15)
N40.046 (2)0.054 (3)0.037 (2)0.003 (2)0.0062 (19)0.007 (2)
O10.0382 (18)0.053 (2)0.0251 (16)0.0018 (14)0.0138 (13)0.0037 (13)
O20.0297 (17)0.054 (2)0.0287 (16)0.0045 (14)0.0035 (13)0.0102 (15)
C10.025 (2)0.026 (2)0.027 (2)0.0062 (17)0.0074 (17)0.0016 (18)
C20.026 (2)0.029 (2)0.025 (2)0.0042 (18)0.0035 (18)0.0014 (18)
C30.025 (2)0.040 (3)0.027 (2)0.0044 (18)0.0067 (18)0.0038 (18)
C40.028 (2)0.044 (3)0.040 (3)0.000 (2)0.009 (2)0.001 (2)
C50.033 (3)0.064 (4)0.069 (4)0.011 (2)0.020 (3)0.004 (3)
C60.030 (3)0.084 (4)0.076 (4)0.002 (3)0.030 (3)0.007 (3)
C70.032 (3)0.067 (4)0.061 (3)0.001 (2)0.022 (2)0.014 (3)
C80.029 (2)0.043 (3)0.037 (3)0.006 (2)0.011 (2)0.002 (2)
C90.033 (3)0.046 (3)0.040 (3)0.004 (2)0.012 (2)0.006 (2)
C100.055 (3)0.039 (3)0.060 (3)0.002 (2)0.016 (3)0.002 (3)
C110.041 (3)0.042 (3)0.044 (3)0.004 (2)0.014 (2)0.009 (2)
C120.044 (3)0.057 (3)0.028 (2)0.006 (2)0.019 (2)0.004 (2)
C130.041 (3)0.052 (3)0.033 (2)0.005 (2)0.023 (2)0.009 (2)
C140.035 (2)0.038 (3)0.027 (2)0.0020 (19)0.0093 (19)0.0038 (19)
C150.029 (2)0.041 (3)0.024 (2)0.0011 (19)0.0041 (17)0.0010 (19)
C160.024 (2)0.035 (2)0.027 (2)0.0026 (18)0.0048 (18)0.0045 (19)
C170.029 (2)0.033 (3)0.030 (2)0.0006 (18)0.0132 (19)0.0038 (19)
C180.033 (2)0.050 (3)0.040 (3)0.003 (2)0.018 (2)0.010 (2)
C190.039 (3)0.066 (4)0.050 (3)0.013 (2)0.031 (2)0.010 (3)
C200.056 (3)0.061 (4)0.042 (3)0.004 (3)0.031 (3)0.006 (2)
C210.038 (3)0.054 (3)0.032 (2)0.000 (2)0.016 (2)0.006 (2)
C220.033 (2)0.029 (2)0.033 (2)0.0053 (18)0.0175 (19)0.0019 (19)
Geometric parameters (Å, º) top
Cu1—N61.950 (3)C7—C81.390 (6)
Cu1—N21.958 (3)C7—H70.9300
Cu1—N11.994 (3)C8—C91.511 (6)
Cu1—N52.122 (3)C9—H90.9800
Cu1—N32.383 (3)C10—C111.533 (6)
N1—C11.349 (5)C10—H10A0.9700
N1—C221.415 (5)C10—H10B0.9700
N2—C21.338 (5)C11—H11A0.9700
N2—C31.427 (5)C11—H11B0.9700
N3—C121.465 (5)C12—C131.522 (7)
N3—C111.475 (6)C12—H12A0.9700
N3—C91.498 (5)C12—H12B0.9700
N5—C131.478 (5)C13—H13A0.9700
N5—C141.483 (5)C13—H13B0.9700
N5—H50.9100C14—C151.507 (6)
N6—C161.271 (5)C14—H14A0.9700
N6—C151.468 (5)C14—H14B0.9700
N4—C91.446 (6)C15—H15A0.9700
N4—C101.473 (6)C15—H15B0.9700
N4—H4A0.8600C16—C171.456 (6)
O1—C11.239 (5)C16—H160.9300
O2—C21.237 (5)C17—C221.409 (5)
C1—C21.556 (6)C17—C181.410 (6)
C3—C41.396 (6)C18—C191.366 (6)
C3—C81.404 (6)C18—H180.9300
C4—C51.383 (6)C19—C201.385 (7)
C4—H40.9300C19—H190.9300
C5—C61.375 (7)C20—C211.379 (6)
C5—H5A0.9300C20—H200.9300
C6—C71.374 (7)C21—C221.405 (6)
C6—H60.9300C21—H210.9300
N6—Cu1—N2173.14 (14)N4—C9—H9107.6
N6—Cu1—N191.47 (13)N3—C9—H9107.6
N2—Cu1—N182.72 (13)C8—C9—H9107.6
N6—Cu1—N583.33 (13)N4—C10—C11105.9 (4)
N2—Cu1—N5100.43 (13)N4—C10—H10A110.6
N1—Cu1—N5155.18 (14)C11—C10—H10A110.6
N6—Cu1—N398.02 (13)N4—C10—H10B110.6
N2—Cu1—N388.42 (13)C11—C10—H10B110.6
N1—Cu1—N3127.12 (13)H10A—C10—H10B108.7
N5—Cu1—N377.69 (13)N3—C11—C10102.1 (4)
C1—N1—C22120.5 (3)N3—C11—H11A111.4
C1—N1—Cu1111.2 (3)C10—C11—H11A111.4
C22—N1—Cu1127.3 (3)N3—C11—H11B111.4
C2—N2—C3120.5 (3)C10—C11—H11B111.4
C2—N2—Cu1113.1 (3)H11A—C11—H11B109.2
C3—N2—Cu1125.9 (3)N3—C12—C13111.4 (3)
C12—N3—C11114.2 (3)N3—C12—H12A109.4
C12—N3—C9113.9 (3)C13—C12—H12A109.4
C11—N3—C9100.7 (3)N3—C12—H12B109.4
C12—N3—Cu1107.6 (3)C13—C12—H12B109.4
C11—N3—Cu1111.5 (3)H12A—C12—H12B108.0
C9—N3—Cu1108.7 (2)N5—C13—C12111.6 (3)
C13—N5—C14114.5 (3)N5—C13—H13A109.3
C13—N5—Cu1113.5 (3)C12—C13—H13A109.3
C14—N5—Cu1106.9 (2)N5—C13—H13B109.3
C13—N5—H5107.2C12—C13—H13B109.3
C14—N5—H5107.2H13A—C13—H13B108.0
Cu1—N5—H5107.2N5—C14—C15110.3 (3)
C16—N6—C15118.7 (3)N5—C14—H14A109.6
C16—N6—Cu1127.8 (3)C15—C14—H14A109.6
C15—N6—Cu1113.4 (3)N5—C14—H14B109.6
C9—N4—C10105.6 (4)C15—C14—H14B109.6
C9—N4—H4A127.2H14A—C14—H14B108.1
C10—N4—H4A127.2N6—C15—C14107.7 (3)
O1—C1—N1128.6 (4)N6—C15—H15A110.2
O1—C1—C2117.7 (3)C14—C15—H15A110.2
N1—C1—C2113.7 (3)N6—C15—H15B110.2
O2—C2—N2129.0 (4)C14—C15—H15B110.2
O2—C2—C1118.1 (4)H15A—C15—H15B108.5
N2—C2—C1112.6 (3)N6—C16—C17126.7 (4)
C4—C3—C8119.4 (4)N6—C16—H16116.6
C4—C3—N2122.6 (4)C17—C16—H16116.6
C8—C3—N2118.0 (4)C22—C17—C18119.7 (4)
C5—C4—C3120.4 (4)C22—C17—C16125.3 (4)
C5—C4—H4119.8C18—C17—C16115.0 (4)
C3—C4—H4119.8C19—C18—C17121.5 (4)
C6—C5—C4120.4 (5)C19—C18—H18119.3
C6—C5—H5A119.8C17—C18—H18119.3
C4—C5—H5A119.8C18—C19—C20118.8 (4)
C7—C6—C5119.5 (5)C18—C19—H19120.6
C7—C6—H6120.2C20—C19—H19120.6
C5—C6—H6120.2C21—C20—C19121.3 (4)
C6—C7—C8121.8 (5)C21—C20—H20119.4
C6—C7—H7119.1C19—C20—H20119.4
C8—C7—H7119.1C20—C21—C22121.1 (4)
C7—C8—C3118.5 (4)C20—C21—H21119.4
C7—C8—C9118.7 (4)C22—C21—H21119.4
C3—C8—C9122.8 (4)C21—C22—C17117.5 (4)
N4—C9—N3103.3 (3)C21—C22—N1122.7 (4)
N4—C9—C8115.3 (4)C17—C22—N1119.7 (4)
N3—C9—C8115.1 (4)
N6—Cu1—N1—C1154.4 (3)N2—C3—C4—C5177.3 (4)
N2—Cu1—N1—C121.9 (3)C3—C4—C5—C61.8 (8)
N5—Cu1—N1—C177.2 (4)C4—C5—C6—C70.7 (8)
N3—Cu1—N1—C1104.4 (3)C5—C6—C7—C80.9 (9)
N6—Cu1—N1—C2213.6 (3)C6—C7—C8—C31.6 (8)
N2—Cu1—N1—C22170.1 (3)C6—C7—C8—C9178.5 (5)
N5—Cu1—N1—C2290.8 (4)C4—C3—C8—C70.5 (6)
N3—Cu1—N1—C2287.6 (3)N2—C3—C8—C7179.0 (4)
N1—Cu1—N2—C223.0 (3)C4—C3—C8—C9179.5 (4)
N5—Cu1—N2—C2132.1 (3)N2—C3—C8—C91.0 (6)
N3—Cu1—N2—C2150.8 (3)C10—N4—C9—N333.6 (5)
N1—Cu1—N2—C3165.1 (3)C10—N4—C9—C8160.1 (4)
N5—Cu1—N2—C339.9 (3)C12—N3—C9—N4170.2 (3)
N3—Cu1—N2—C337.3 (3)C11—N3—C9—N447.5 (4)
N6—Cu1—N3—C1273.0 (3)Cu1—N3—C9—N469.8 (3)
N2—Cu1—N3—C12109.3 (3)C12—N3—C9—C863.3 (5)
N1—Cu1—N3—C12171.0 (2)C11—N3—C9—C8174.0 (4)
N5—Cu1—N3—C128.3 (3)Cu1—N3—C9—C856.7 (4)
N6—Cu1—N3—C1153.0 (3)C7—C8—C9—N4119.6 (5)
N2—Cu1—N3—C11124.7 (3)C3—C8—C9—N460.3 (6)
N1—Cu1—N3—C1145.0 (3)C7—C8—C9—N3120.2 (5)
N5—Cu1—N3—C11134.3 (3)C3—C8—C9—N359.8 (6)
N6—Cu1—N3—C9163.1 (3)C9—N4—C10—C117.4 (5)
N2—Cu1—N3—C914.5 (3)C12—N3—C11—C10163.9 (4)
N1—Cu1—N3—C965.1 (3)C9—N3—C11—C1041.4 (4)
N5—Cu1—N3—C9115.5 (3)Cu1—N3—C11—C1073.8 (4)
N6—Cu1—N5—C13117.0 (3)N4—C10—C11—N321.8 (5)
N2—Cu1—N5—C1368.8 (3)C11—N3—C12—C13155.8 (4)
N1—Cu1—N5—C13164.1 (3)C9—N3—C12—C1389.2 (4)
N3—Cu1—N5—C1317.2 (3)Cu1—N3—C12—C1331.4 (4)
N6—Cu1—N5—C1410.3 (2)C14—N5—C13—C1282.5 (4)
N2—Cu1—N5—C14163.9 (2)Cu1—N5—C13—C1240.7 (4)
N1—Cu1—N5—C1468.7 (4)N3—C12—C13—N548.5 (5)
N3—Cu1—N5—C14110.1 (3)C13—N5—C14—C1592.9 (4)
N1—Cu1—N6—C164.4 (4)Cu1—N5—C14—C1533.8 (4)
N5—Cu1—N6—C16160.0 (4)C16—N6—C15—C14137.8 (4)
N3—Cu1—N6—C16123.5 (4)Cu1—N6—C15—C1438.5 (4)
N1—Cu1—N6—C15171.5 (3)N5—C14—C15—N647.4 (4)
N5—Cu1—N6—C1515.9 (3)C15—N6—C16—C17179.6 (4)
N3—Cu1—N6—C1560.6 (3)Cu1—N6—C16—C174.7 (6)
C22—N1—C1—O14.3 (6)N6—C16—C17—C227.9 (7)
Cu1—N1—C1—O1164.7 (3)N6—C16—C17—C18170.7 (4)
C22—N1—C1—C2173.9 (3)C22—C17—C18—C191.9 (7)
Cu1—N1—C1—C217.2 (4)C16—C17—C18—C19176.8 (4)
C3—N2—C2—O25.4 (7)C17—C18—C19—C200.1 (7)
Cu1—N2—C2—O2167.0 (4)C18—C19—C20—C211.4 (7)
C3—N2—C2—C1168.4 (3)C19—C20—C21—C221.2 (7)
Cu1—N2—C2—C119.2 (4)C20—C21—C22—C170.6 (6)
O1—C1—C2—O22.9 (6)C20—C21—C22—N1179.1 (4)
N1—C1—C2—O2175.5 (4)C18—C17—C22—C212.1 (6)
O1—C1—C2—N2177.5 (4)C16—C17—C22—C21176.5 (4)
N1—C1—C2—N20.9 (5)C18—C17—C22—N1179.4 (4)
C2—N2—C3—C443.7 (6)C16—C17—C22—N12.1 (6)
Cu1—N2—C3—C4127.7 (4)C1—N1—C22—C2128.5 (6)
C2—N2—C3—C8137.9 (4)Cu1—N1—C22—C21164.5 (3)
Cu1—N2—C3—C850.7 (5)C1—N1—C22—C17153.0 (4)
C8—C3—C4—C51.1 (7)Cu1—N1—C22—C1714.0 (5)
 

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