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The title complex, [Cu2(C23H26Cl2N4O2)](ClO4)2, has been synthesized by condensation between N,N′-dimethyl-N,N′-bis­(3-formyl-5-chloro­salicyl­idene)ethyl­enediamine and 1,3-propane­diamine in the presence of copper(II). The complex is a phenol-based macrocyclic dinuclear complex, with the two CuII ions in N(amine)2O2 and N(imine)2O2 sites, and a Cu...Cu separation of 3.0138 (14) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035859/hg2075sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035859/hg2075Isup2.hkl
Contains datablock I

CCDC reference: 624712

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.061
  • wR factor = 0.126
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 5798 Count of symmetry unique reflns 3092 Completeness (_total/calc) 187.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2706 Fraction of Friedel pairs measured 0.875 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 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 1 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: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[µ-rel-(3R,6S)-10,22-Dichloro-3,6-dimethyl-3,6,14,18- tetraazatricyclo[18.3.1.18,12]pentacosa-1(24),8,10,12(25),13,18,20,22- octane-24,25-diolato- κ4N3,N6,O24,O25:κ4N14,N18,O24,O25]dicopper(II) perchlorate top
Crystal data top
[Cu2(C23H26Cl2N4O2)](ClO4)2F(000) = 796
Mr = 787.36Dx = 1.762 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2271 reflections
a = 8.7105 (16) Åθ = 2.3–19.9°
b = 9.5778 (18) ŵ = 1.85 mm1
c = 18.104 (3) ÅT = 298 K
β = 100.761 (18)°Needle, dark green
V = 1483.8 (5) Å30.32 × 0.26 × 0.24 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5798 independent reflections
Radiation source: sealed tube4438 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 26.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.57, Tmax = 0.64k = 1111
15477 measured reflectionsl = 2222
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)] = 0.061H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.05P)2 + 1.88P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5798 reflectionsΔρmax = 0.37 e Å3
390 parametersΔρmin = 0.67 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (2)
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
C10.2472 (9)0.7053 (9)0.6394 (4)0.0398 (17)
C20.2562 (8)0.6453 (8)0.5704 (4)0.0433 (19)
C30.1295 (9)0.6533 (8)0.5112 (5)0.0440 (19)
H30.13550.61320.46500.053*
C40.0063 (8)0.7213 (9)0.5210 (4)0.0415 (17)
C50.0153 (11)0.7813 (10)0.5899 (4)0.055 (2)
H50.10620.82680.59650.066*
C60.1114 (9)0.7732 (8)0.6492 (4)0.0447 (19)
C70.0856 (8)0.8166 (9)0.7239 (4)0.0425 (16)
H7A0.01560.86190.71800.051*
H7B0.08140.73360.75420.051*
C80.1637 (9)0.9629 (10)0.8358 (4)0.0471 (19)
H8A0.05830.93560.83960.057*
H8B0.16631.06410.83390.057*
C90.2733 (9)0.9153 (9)0.9060 (4)0.048 (2)
H9A0.28140.98700.94440.058*
H9B0.23290.83120.92530.058*
C100.5196 (8)0.7931 (8)0.9381 (4)0.0456 (19)
H10A0.46540.70420.93450.055*
H10B0.52460.82800.98880.055*
C110.6974 (9)0.6902 (9)0.8630 (5)0.0470 (19)
C120.6827 (9)0.7688 (9)0.9259 (4)0.048 (2)
C130.8029 (9)0.7700 (9)0.9883 (5)0.049 (2)
H130.79310.82261.03040.059*
C140.9377 (8)0.6925 (8)0.9879 (4)0.0410 (17)
C150.9523 (8)0.6139 (8)0.9251 (4)0.0429 (18)
H151.04250.56210.92480.051*
C160.8322 (8)0.6128 (8)0.8626 (4)0.0417 (17)
C170.8539 (9)0.5206 (8)0.8005 (4)0.0413 (17)
H170.94750.47130.80760.050*
C180.8198 (9)0.3991 (9)0.6872 (4)0.0449 (18)
H18A0.77640.30770.69370.054*
H18B0.93240.39230.70210.054*
C190.7805 (9)0.4381 (10)0.6048 (4)0.050 (2)
H19A0.80730.53510.59850.060*
H19B0.84120.38110.57650.060*
C200.6082 (8)0.4162 (8)0.5748 (4)0.0445 (18)
H20A0.58890.42290.52040.053*
H20B0.57900.32310.58800.053*
C210.3835 (8)0.5497 (7)0.5598 (4)0.0364 (16)
H210.37030.50460.51350.044*
C220.2086 (10)1.0351 (8)0.7190 (4)0.049 (2)
H22A0.19651.01120.66670.074*
H22B0.30851.07840.73530.074*
H22C0.12731.09860.72600.074*
C230.5420 (9)1.0083 (9)0.8948 (5)0.052 (2)
H23A0.53371.06120.93890.078*
H23B0.51621.06680.85120.078*
H23C0.64690.97440.89880.078*
Cl10.1592 (2)0.7410 (2)0.44426 (10)0.0467 (5)
Cl21.0895 (2)0.7020 (2)1.06212 (11)0.0495 (5)
Cl30.3256 (2)0.42379 (19)0.82301 (10)0.0408 (4)
Cl40.6355 (2)0.9702 (2)0.67227 (11)0.0434 (5)
Cu10.40054 (11)0.80931 (9)0.78585 (6)0.0478 (3)
Cu20.55938 (10)0.59222 (9)0.70586 (5)0.0411 (2)
N10.1985 (7)0.9071 (8)0.7634 (4)0.0456 (16)
N20.4311 (7)0.8870 (7)0.8877 (4)0.0430 (15)
N30.7610 (7)0.4990 (6)0.7380 (4)0.0427 (15)
N40.5081 (7)0.5211 (7)0.6054 (4)0.0473 (17)
O10.3721 (6)0.7059 (6)0.6947 (3)0.0438 (12)
O20.5789 (6)0.6926 (6)0.8033 (3)0.0442 (12)
O30.3856 (6)0.4132 (6)0.7563 (3)0.0488 (14)
O40.4523 (6)0.4115 (6)0.8863 (3)0.0507 (14)
O50.2127 (5)0.3225 (6)0.8336 (3)0.0468 (13)
O60.2675 (6)0.5596 (5)0.8279 (3)0.0423 (12)
O70.5757 (6)0.9821 (6)0.7381 (3)0.0449 (13)
O80.6706 (6)0.8244 (6)0.6563 (3)0.0487 (13)
O90.7588 (6)1.0608 (6)0.6716 (3)0.0455 (13)
O100.5169 (6)1.0258 (6)0.6192 (3)0.0473 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (4)0.044 (4)0.035 (4)0.002 (3)0.023 (3)0.000 (3)
C20.038 (4)0.041 (4)0.047 (5)0.015 (3)0.003 (3)0.013 (3)
C30.044 (4)0.044 (4)0.046 (5)0.016 (3)0.014 (4)0.017 (3)
C40.035 (4)0.061 (5)0.028 (4)0.009 (3)0.005 (3)0.001 (3)
C50.069 (5)0.060 (6)0.035 (4)0.003 (4)0.007 (4)0.010 (4)
C60.047 (4)0.049 (5)0.041 (4)0.011 (3)0.014 (3)0.014 (3)
C70.040 (4)0.044 (4)0.046 (4)0.002 (4)0.016 (3)0.015 (4)
C80.043 (4)0.052 (5)0.046 (5)0.015 (4)0.004 (3)0.002 (4)
C90.058 (5)0.045 (5)0.044 (4)0.023 (4)0.017 (4)0.012 (4)
C100.048 (4)0.040 (4)0.044 (4)0.023 (4)0.004 (3)0.001 (3)
C110.039 (4)0.052 (5)0.049 (5)0.006 (4)0.005 (3)0.009 (4)
C120.037 (4)0.063 (6)0.040 (4)0.022 (4)0.002 (3)0.012 (4)
C130.043 (4)0.050 (5)0.043 (4)0.003 (3)0.019 (3)0.008 (3)
C140.045 (4)0.041 (4)0.037 (4)0.011 (3)0.010 (3)0.001 (3)
C150.042 (4)0.037 (4)0.050 (5)0.006 (3)0.007 (3)0.011 (3)
C160.033 (3)0.041 (4)0.054 (5)0.012 (3)0.018 (3)0.008 (4)
C170.048 (4)0.039 (4)0.040 (4)0.001 (3)0.016 (3)0.003 (3)
C180.041 (4)0.044 (5)0.052 (5)0.016 (3)0.014 (3)0.003 (4)
C190.051 (5)0.058 (6)0.045 (5)0.001 (4)0.019 (4)0.018 (4)
C200.049 (4)0.044 (4)0.039 (4)0.018 (4)0.004 (3)0.004 (3)
C210.046 (4)0.026 (4)0.035 (4)0.011 (3)0.003 (3)0.006 (3)
C220.058 (5)0.055 (5)0.037 (4)0.021 (4)0.011 (4)0.011 (3)
C230.048 (4)0.065 (6)0.047 (5)0.005 (4)0.017 (4)0.021 (4)
Cl10.0451 (10)0.0469 (10)0.0411 (10)0.0149 (8)0.0106 (8)0.0169 (8)
Cl20.0478 (10)0.0468 (11)0.0481 (11)0.0046 (9)0.0062 (8)0.0056 (9)
Cl30.0392 (9)0.0386 (10)0.0466 (10)0.0079 (7)0.0132 (8)0.0027 (8)
Cl40.0438 (10)0.0452 (11)0.0413 (11)0.0066 (8)0.0078 (8)0.0175 (8)
Cu10.0444 (5)0.0405 (6)0.0545 (6)0.0108 (4)0.0011 (4)0.0105 (4)
Cu20.0383 (5)0.0448 (5)0.0378 (5)0.0071 (4)0.0011 (4)0.0025 (4)
N10.045 (3)0.055 (4)0.039 (4)0.005 (3)0.014 (3)0.006 (3)
N20.040 (3)0.042 (4)0.049 (4)0.014 (3)0.012 (3)0.003 (3)
N30.042 (3)0.038 (4)0.051 (4)0.006 (3)0.015 (3)0.013 (3)
N40.046 (4)0.052 (4)0.047 (4)0.022 (3)0.016 (3)0.014 (3)
O10.042 (3)0.049 (3)0.045 (3)0.002 (2)0.021 (2)0.011 (3)
O20.038 (3)0.048 (3)0.048 (3)0.015 (2)0.011 (2)0.002 (3)
O30.054 (3)0.050 (3)0.047 (3)0.012 (3)0.020 (3)0.008 (3)
O40.052 (3)0.039 (3)0.057 (3)0.008 (2)0.001 (3)0.015 (3)
O50.044 (3)0.046 (3)0.055 (3)0.001 (3)0.021 (2)0.008 (3)
O60.054 (3)0.027 (3)0.051 (3)0.011 (2)0.025 (2)0.011 (2)
O70.042 (3)0.044 (3)0.045 (3)0.011 (2)0.001 (2)0.011 (3)
O80.043 (3)0.053 (3)0.052 (3)0.009 (3)0.017 (2)0.002 (3)
O90.050 (3)0.045 (3)0.047 (3)0.005 (2)0.024 (2)0.006 (2)
O100.047 (3)0.056 (3)0.037 (3)0.006 (2)0.003 (2)0.010 (2)
Geometric parameters (Å, º) top
C1—O11.334 (9)C17—H170.9300
C1—C21.390 (10)C18—N31.482 (9)
C1—C61.390 (10)C18—C191.515 (11)
C2—C31.390 (11)C18—H18A0.9700
C2—C211.478 (9)C18—H18B0.9700
C3—C41.390 (10)C19—C201.512 (11)
C3—H30.9300C19—H19A0.9700
C4—C51.390 (10)C19—H19B0.9700
C4—Cl11.745 (7)C20—N41.502 (9)
C5—C61.390 (11)C20—H20A0.9700
C5—H50.9300C20—H20B0.9700
C6—C71.473 (9)C21—N41.265 (9)
C7—N11.403 (9)C21—H210.9300
C7—H7A0.9700C22—N11.478 (10)
C7—H7B0.9700C22—H22A0.9600
C8—N11.496 (10)C22—H22B0.9600
C8—C91.511 (10)C22—H22C0.9600
C8—H8A0.9700C23—N21.501 (10)
C8—H8B0.9700C23—H23A0.9600
C9—N21.498 (9)C23—H23B0.9600
C9—H9A0.9700C23—H23C0.9600
C9—H9B0.9700Cl3—O61.405 (5)
C10—N21.405 (9)Cl3—O31.406 (5)
C10—C121.497 (10)Cl3—O51.419 (5)
C10—H10A0.9700Cl3—O41.440 (6)
C10—H10B0.9700Cl4—O101.380 (5)
C11—O21.349 (9)Cl4—O91.383 (5)
C11—C121.390 (11)Cl4—O71.391 (6)
C11—C161.390 (10)Cl4—O81.470 (6)
C12—C131.390 (10)Cu1—O21.892 (5)
C13—C141.390 (11)Cu1—O11.900 (5)
C13—H130.9300Cu1—N21.960 (6)
C14—C151.390 (10)Cu1—N11.968 (6)
C14—Cl21.702 (7)Cu2—N41.915 (6)
C15—C161.390 (10)Cu2—O11.941 (5)
C15—H150.9300Cu2—N31.960 (6)
C16—C171.469 (10)Cu2—O21.988 (5)
C17—N31.279 (10)
O1—C1—C2120.1 (6)C20—C19—H19B109.6
O1—C1—C6119.7 (6)C18—C19—H19B109.6
C2—C1—C6120.0 (7)H19A—C19—H19B108.1
C3—C2—C1120.0 (7)N4—C20—C19112.4 (6)
C3—C2—C21116.2 (7)N4—C20—H20A109.1
C1—C2—C21122.9 (7)C19—C20—H20A109.1
C4—C3—C2120.0 (7)N4—C20—H20B109.1
C4—C3—H3120.0C19—C20—H20B109.1
C2—C3—H3120.0H20A—C20—H20B107.9
C5—C4—C3120.0 (7)N4—C21—C2128.4 (7)
C5—C4—Cl1120.5 (6)N4—C21—H21115.8
C3—C4—Cl1119.4 (5)C2—C21—H21115.8
C4—C5—C6120.0 (8)N1—C22—H22A109.5
C4—C5—H5120.0N1—C22—H22B109.5
C6—C5—H5120.0H22A—C22—H22B109.5
C5—C6—C1120.0 (7)N1—C22—H22C109.5
C5—C6—C7117.2 (7)H22A—C22—H22C109.5
C1—C6—C7121.9 (7)H22B—C22—H22C109.5
N1—C7—C6115.5 (6)N2—C23—H23A109.5
N1—C7—H7A108.4N2—C23—H23B109.5
C6—C7—H7A108.4H23A—C23—H23B109.5
N1—C7—H7B108.4N2—C23—H23C109.5
C6—C7—H7B108.4H23A—C23—H23C109.5
H7A—C7—H7B107.5H23B—C23—H23C109.5
N1—C8—C9115.4 (6)O6—Cl3—O3108.5 (3)
N1—C8—H8A108.4O6—Cl3—O5111.0 (3)
C9—C8—H8A108.4O3—Cl3—O5116.4 (4)
N1—C8—H8B108.4O6—Cl3—O4104.9 (3)
C9—C8—H8B108.4O3—Cl3—O4109.0 (3)
H8A—C8—H8B107.5O5—Cl3—O4106.5 (3)
N2—C9—C8109.2 (6)O10—Cl4—O9103.5 (3)
N2—C9—H9A109.8O10—Cl4—O7102.3 (3)
C8—C9—H9A109.8O9—Cl4—O7111.8 (3)
N2—C9—H9B109.8O10—Cl4—O8112.7 (3)
C8—C9—H9B109.8O9—Cl4—O8113.9 (3)
H9A—C9—H9B108.3O7—Cl4—O8111.8 (3)
N2—C10—C12115.1 (7)O2—Cu1—O178.9 (2)
N2—C10—H10A108.5O2—Cu1—N296.0 (2)
C12—C10—H10A108.5O1—Cu1—N2170.9 (3)
N2—C10—H10B108.5O2—Cu1—N1172.1 (3)
C12—C10—H10B108.5O1—Cu1—N195.9 (3)
H10A—C10—H10B107.5N2—Cu1—N188.4 (3)
O2—C11—C12118.3 (7)N4—Cu2—O193.3 (2)
O2—C11—C16121.7 (7)N4—Cu2—N399.0 (3)
C12—C11—C16120.0 (7)O1—Cu2—N3167.5 (2)
C11—C12—C13120.0 (7)N4—Cu2—O2168.7 (2)
C11—C12—C10116.1 (7)O1—Cu2—O275.6 (2)
C13—C12—C10118.0 (7)N3—Cu2—O291.9 (2)
C14—C13—C12120.0 (8)C7—N1—C22110.0 (6)
C14—C13—H13120.0C7—N1—C8115.4 (6)
C12—C13—H13120.0C22—N1—C8102.9 (6)
C15—C14—C13120.0 (7)C7—N1—Cu1109.0 (5)
C15—C14—Cl2119.9 (6)C22—N1—Cu1111.4 (5)
C13—C14—Cl2120.0 (6)C8—N1—Cu1108.0 (5)
C16—C15—C14120.0 (7)C10—N2—C9112.8 (6)
C16—C15—H15120.0C10—N2—C23100.0 (6)
C14—C15—H15120.0C9—N2—C23116.3 (6)
C15—C16—C11120.0 (7)C10—N2—Cu1109.3 (5)
C15—C16—C17116.3 (6)C9—N2—Cu1108.0 (5)
C11—C16—C17123.6 (7)C23—N2—Cu1110.3 (5)
N3—C17—C16128.6 (7)C17—N3—C18114.8 (6)
N3—C17—H17115.7C17—N3—Cu2124.9 (5)
C16—C17—H17115.7C18—N3—Cu2120.3 (5)
N3—C18—C19114.3 (6)C21—N4—C20113.0 (6)
N3—C18—H18A108.7C21—N4—Cu2124.3 (5)
C19—C18—H18A108.7C20—N4—Cu2122.6 (5)
N3—C18—H18B108.7C1—O1—Cu1127.6 (5)
C19—C18—H18B108.7C1—O1—Cu2128.8 (5)
H18A—C18—H18B107.6Cu1—O1—Cu2103.4 (2)
C20—C19—C18110.2 (7)C11—O2—Cu1128.7 (5)
C20—C19—H19A109.6C11—O2—Cu2129.0 (5)
C18—C19—H19A109.6Cu1—O2—Cu2101.9 (2)
 

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