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The title mononuclear copper(II) compound, [CuCl(C16H22­N4)]­ClO4, shows a slightly tetrahedrally distorted square-pyramidal coordination with the chlorine ligand at the apical position. The directions of the two N-Me bond axes are syn to the Cu-Cl bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005588/qa0279sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005588/qa0279Isup2.hkl
Contains datablock I

Comment top

DNA degradation by the copper(II) complexes with tripodal ligands has been investigated by one (YN) of the authors (Kobayashi et al., 1996; Kobayashi et al., 1998). The structure of [Cu(mep)Cl]ClO4, (I), where mep is 1,6-bis(2-pyridylmethyl)-2,5-diazahexane, is reported here.

Experimental top

The ligand and its chlorocopper(II) complex were prepared as described previously (Okuno et al., 1997). Crystals of the title compound were grown from a methanol solution.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and fixed with U(H) = 1.2Ueq(parent atom). The maximum residual density was located 0.99 Å from the Cu1 atom.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
[CuCl(C16H22N4)]ClO4Dx = 1.610 Mg m3
Mr = 468.83Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21/cCell parameters from 25 reflections
a = 11.044 (2) Åθ = 10–15°
b = 11.085 (1) ŵ = 1.44 mm1
c = 15.858 (1) ÅT = 299 K
β = 95.100 (9)°Prism, blue
V = 1933.8 (4) Å30.6 × 0.5 × 0.2 mm
Z = 4
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.028
θ–2θ scansθmax = 27.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 014
Tmin = 0.365, Tmax = 0.764k = 014
4916 measured reflectionsl = 2121
4445 independent reflections3 standard reflections every 100 reflections
3426 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.05(Fo2 + 2Fc2)/3)2]
wR(F2) = 0.122(Δ/σ)max = 0.001
S = 1.51Δρmax = 0.98 e Å3
4445 reflectionsΔρmin = 0.68 e Å3
244 parameters
Crystal data top
[CuCl(C16H22N4)]ClO4V = 1933.8 (4) Å3
Mr = 468.83Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.044 (2) ŵ = 1.44 mm1
b = 11.085 (1) ÅT = 299 K
c = 15.858 (1) Å0.6 × 0.5 × 0.2 mm
β = 95.100 (9)°
Data collection top
Rigaku AFC-5S
diffractometer
3426 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.028
Tmin = 0.365, Tmax = 0.7643 standard reflections every 100 reflections
4916 measured reflections intensity decay: none
4445 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049244 parameters
wR(F2) = 0.122H-atom parameters not refined
S = 1.51Δρmax = 0.98 e Å3
4445 reflectionsΔρmin = 0.68 e Å3
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.71254 (3)0.16092 (3)0.27961 (2)0.02884 (10)
Cl10.55658 (8)0.22147 (8)0.17090 (5)0.0431 (2)
Cl21.12933 (9)0.14997 (8)0.39210 (5)0.0443 (2)
O11.1330 (8)0.0417 (4)0.4312 (3)0.193 (3)
O21.0079 (4)0.1912 (6)0.3864 (3)0.147 (2)
O31.2025 (4)0.2331 (4)0.4416 (2)0.089 (1)
O41.1616 (4)0.1408 (4)0.3088 (2)0.102 (2)
N10.7187 (3)0.3226 (2)0.3429 (2)0.0351 (7)
N20.6194 (3)0.1125 (3)0.3819 (2)0.0388 (7)
N30.7537 (3)0.0188 (2)0.2757 (2)0.0374 (7)
N40.8456 (2)0.1720 (2)0.1994 (2)0.0334 (7)
C10.7219 (3)0.4352 (3)0.3114 (2)0.0414 (9)
C20.7028 (4)0.5365 (3)0.3591 (3)0.050 (1)
C30.6812 (4)0.5217 (4)0.4423 (3)0.058 (1)
C40.6774 (4)0.4067 (4)0.4761 (2)0.052 (1)
C50.6960 (3)0.3091 (3)0.4243 (2)0.0391 (9)
C60.6870 (4)0.1798 (3)0.4518 (2)0.0451 (10)
C70.6300 (4)0.0196 (3)0.3956 (2)0.051 (1)
C80.7457 (4)0.0652 (3)0.3630 (2)0.051 (1)
C90.8790 (3)0.0306 (3)0.2500 (2)0.0429 (9)
C100.9022 (3)0.0669 (3)0.1882 (2)0.0369 (8)
C110.9808 (4)0.0515 (4)0.1257 (3)0.051 (1)
C121.0050 (4)0.1490 (4)0.0759 (2)0.053 (1)
C130.9502 (3)0.2579 (4)0.0889 (2)0.048 (1)
C140.8690 (3)0.2653 (3)0.1499 (2)0.0414 (9)
C150.4893 (4)0.1493 (4)0.3745 (3)0.059 (1)
C160.6678 (4)0.0813 (3)0.2130 (2)0.048 (1)
H10.73820.44550.25330.0497*
H20.70450.61560.33460.0600*
H30.66870.59080.47700.0699*
H40.66220.39490.53420.0629*
H50.64450.17510.50190.0542*
H60.76700.14630.46320.0542*
H70.63120.03670.45500.0611*
H80.56170.05930.36590.0611*
H90.74520.15180.36230.0611*
H100.81430.03720.39920.0611*
H110.93620.02370.29900.0515*
H120.88810.10790.22400.0515*
H131.01760.02550.11720.0608*
H141.05970.14090.03240.0632*
H150.96810.32750.05610.0570*
H160.82760.34030.15710.0497*
H170.48340.23440.36340.0703*
H180.44610.10590.32890.0703*
H190.45450.13160.42640.0703*
H200.58660.07400.22960.0580*
H210.67190.04540.15820.0580*
H220.68920.16510.21050.0580*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0317 (2)0.0244 (2)0.0310 (2)0.0015 (2)0.0062 (1)0.0025 (1)
Cl10.0383 (4)0.0484 (5)0.0416 (4)0.0066 (4)0.0016 (3)0.0033 (3)
Cl20.0537 (5)0.0364 (4)0.0434 (4)0.0061 (4)0.0082 (4)0.0042 (3)
O10.38 (1)0.058 (3)0.124 (4)0.043 (4)0.067 (5)0.036 (3)
O20.071 (3)0.254 (7)0.115 (4)0.041 (4)0.004 (2)0.076 (4)
O30.089 (3)0.083 (3)0.097 (3)0.036 (2)0.022 (2)0.043 (2)
O40.119 (4)0.124 (4)0.070 (2)0.023 (3)0.042 (2)0.033 (2)
N10.038 (1)0.031 (1)0.036 (1)0.001 (1)0.004 (1)0.000 (1)
N20.045 (2)0.039 (1)0.033 (1)0.003 (1)0.007 (1)0.006 (1)
N30.039 (1)0.029 (1)0.044 (1)0.003 (1)0.004 (1)0.002 (1)
N40.032 (1)0.032 (1)0.037 (1)0.000 (1)0.005 (1)0.003 (1)
C10.042 (2)0.031 (2)0.053 (2)0.004 (1)0.010 (2)0.001 (1)
C20.051 (2)0.030 (2)0.069 (2)0.001 (2)0.007 (2)0.002 (2)
C30.068 (3)0.043 (2)0.064 (2)0.003 (2)0.008 (2)0.019 (2)
C40.071 (3)0.047 (2)0.040 (2)0.004 (2)0.008 (2)0.008 (2)
C50.044 (2)0.038 (2)0.035 (2)0.002 (1)0.001 (1)0.002 (1)
C60.064 (2)0.040 (2)0.031 (2)0.004 (2)0.004 (2)0.003 (1)
C70.073 (3)0.037 (2)0.044 (2)0.012 (2)0.014 (2)0.008 (1)
C80.073 (3)0.030 (2)0.050 (2)0.003 (2)0.006 (2)0.012 (1)
C90.040 (2)0.035 (2)0.054 (2)0.007 (1)0.001 (1)0.004 (1)
C100.032 (2)0.036 (2)0.042 (2)0.000 (1)0.001 (1)0.001 (1)
C110.039 (2)0.050 (2)0.065 (2)0.009 (2)0.012 (2)0.002 (2)
C120.041 (2)0.066 (3)0.053 (2)0.001 (2)0.018 (2)0.002 (2)
C130.041 (2)0.057 (2)0.046 (2)0.006 (2)0.010 (2)0.007 (2)
C140.044 (2)0.038 (2)0.043 (2)0.000 (2)0.009 (1)0.006 (1)
C150.042 (2)0.078 (3)0.058 (2)0.001 (2)0.017 (2)0.015 (2)
C160.051 (2)0.037 (2)0.057 (2)0.009 (2)0.004 (2)0.007 (2)
Geometric parameters (Å, º) top
Cu1—Cl12.421 (1)C4—H40.960
Cu1—N12.053 (3)C5—C61.504 (5)
Cu1—N22.068 (3)C6—H50.960
Cu1—N32.046 (3)C6—H60.960
Cu1—N42.031 (3)C7—C81.507 (6)
Cl2—O11.350 (4)C7—H70.960
Cl2—O21.412 (5)C7—H80.960
Cl2—O31.417 (3)C8—H90.960
Cl2—O41.402 (3)C8—H100.960
N1—C11.347 (4)C9—C101.496 (5)
N1—C51.345 (4)C9—H110.960
N2—C61.481 (4)C9—H120.960
N2—C71.484 (5)C10—C111.385 (5)
N2—C151.488 (5)C11—C121.379 (6)
N3—C81.487 (4)C11—H130.960
N3—C91.483 (5)C12—C131.374 (6)
N3—C161.485 (5)C12—H140.960
N4—C101.341 (4)C13—C141.379 (5)
N4—C141.337 (4)C13—H150.960
C1—C21.381 (5)C14—H160.960
C1—H10.960C15—H170.960
C2—C31.371 (6)C15—H180.960
C2—H20.960C15—H190.960
C3—C41.385 (6)C16—H200.960
C3—H30.960C16—H210.960
C4—C51.384 (5)C16—H220.960
Cu1···O23.556 (5)O3···C12iv3.438 (5)
Cl1···C2i3.520 (4)O3···C3v3.465 (5)
O1···C13ii3.285 (6)O3···C15vi3.553 (6)
O1···C14ii3.322 (6)O3···C16vii3.594 (6)
O1···C8iii3.425 (7)O4···C1ii3.304 (5)
O1···C6iii3.573 (7)O4···C2ii3.374 (5)
O2···N43.333 (5)O4···C103.400 (6)
O2···C13iv3.376 (6)O4···C113.517 (6)
O2···C12iv3.490 (6)C1···C11vii3.586 (5)
O2···C93.494 (7)C2···C11vii3.486 (6)
O2···N13.523 (6)C2···C12vii3.528 (6)
O2···C103.533 (6)C6···C13iv3.539 (5)
Cl1—Cu1—N195.6 (1)N2—C6—H5109.9
Cl1—Cu1—N2105.0 (1)N2—C6—H6109.9
Cl1—Cu1—N3113.3 (1)C5—C6—H5109.9
Cl1—Cu1—N492.6 (1)C5—C6—H6109.9
N1—Cu1—N280.8 (1)H5—C6—H6109.5
N1—Cu1—N3150.1 (1)N2—C7—C8109.8 (3)
N1—Cu1—N4105.0 (1)N2—C7—H7109.4
N2—Cu1—N384.2 (1)N2—C7—H8109.4
N2—Cu1—N4161.0 (1)C8—C7—H7109.4
N3—Cu1—N482.2 (1)C8—C7—H8109.4
O1—Cl2—O2107.9 (5)H7—C7—H8109.5
O1—Cl2—O3109.4 (3)N3—C8—C7109.0 (3)
O1—Cl2—O4111.6 (4)N3—C8—H9109.6
O2—Cl2—O3108.5 (3)N3—C8—H10109.6
O2—Cl2—O4106.4 (3)C7—C8—H9109.6
O3—Cl2—O4112.9 (2)C7—C8—H10109.6
Cu1—N1—C1128.9 (2)H9—C8—H10109.5
Cu1—N1—C5111.8 (2)N3—C9—C10109.5 (3)
C1—N1—C5118.2 (3)N3—C9—H11109.5
Cu1—N2—C6101.7 (2)N3—C9—H12109.5
Cu1—N2—C7109.4 (2)C10—C9—H11109.5
Cu1—N2—C15114.2 (2)C10—C9—H12109.5
C6—N2—C7111.1 (3)H11—C9—H12109.5
C6—N2—C15109.9 (3)N4—C10—C9115.6 (3)
C7—N2—C15110.2 (3)N4—C10—C11122.0 (3)
Cu1—N3—C8106.1 (2)C9—C10—C11122.3 (3)
Cu1—N3—C9108.1 (2)C10—C11—C12118.7 (3)
Cu1—N3—C16110.1 (2)C10—C11—H13120.7
C8—N3—C9111.1 (3)C12—C11—H13120.7
C8—N3—C16112.0 (3)C11—C12—C13119.5 (3)
C9—N3—C16109.3 (3)C11—C12—H14120.3
Cu1—N4—C10113.7 (2)C13—C12—H14120.3
Cu1—N4—C14127.1 (2)C12—C13—C14118.7 (3)
C10—N4—C14118.5 (3)C12—C13—H15120.6
N1—C1—C2122.6 (3)C14—C13—H15120.6
N1—C1—H1118.7N4—C14—C13122.5 (3)
C2—C1—H1118.7N4—C14—H16118.7
C1—C2—C3118.6 (3)C13—C14—H16118.8
C1—C2—H2120.7N2—C15—H17109.5
C3—C2—H2120.7N2—C15—H18109.5
C2—C3—C4119.7 (3)N2—C15—H19109.5
C2—C3—H3120.1H17—C15—H18109.5
C4—C3—H3120.1H17—C15—H19109.5
C3—C4—C5118.6 (3)H18—C15—H19109.5
C3—C4—H4120.7N3—C16—H20109.5
C5—C4—H4120.7N3—C16—H21109.5
N1—C5—C4122.2 (3)N3—C16—H22109.5
N1—C5—C6114.0 (3)H20—C16—H21109.5
C4—C5—C6123.8 (3)H20—C16—H22109.5
N2—C6—C5107.8 (3)H21—C16—H22109.5
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+2, y1/2, z+1/2; (iii) x+2, y, z+1; (iv) x, y+1/2, z+1/2; (v) x+2, y+1, z+1; (vi) x+1, y, z; (vii) x+2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[CuCl(C16H22N4)]ClO4
Mr468.83
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)11.044 (2), 11.085 (1), 15.858 (1)
β (°) 95.100 (9)
V3)1933.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.44
Crystal size (mm)0.6 × 0.5 × 0.2
Data collection
DiffractometerRigaku AFC-5S
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.365, 0.764
No. of measured, independent and
observed [I > 2σ(I)] reflections
4916, 4445, 3426
Rint0.028
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.122, 1.51
No. of reflections4445
No. of parameters244
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.98, 0.68

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), TEXSAN.

Selected bond lengths (Å) top
Cu1—Cl12.421 (1)Cu1—N32.046 (3)
Cu1—N12.053 (3)Cu1—N42.031 (3)
Cu1—N22.068 (3)
 

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