In the title complex, [CuIICl(C14H21N5)]ClO4, the Cu atom is located at the center of a distorted trigonal bipyramid of five coordinating atoms (four N atoms and one Cl atom). Two N atoms are located in axial positions, and the other two N atoms and the Cl atom are in the equatorial plane. The Cu atom is located 0.0670 (2) Å below the equatorial plane.
Supporting information
CCDC reference: 202973
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.069
- Data-to-parameter ratio = 14.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
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.
[1-(benzimidazol-2-ylmethyl)-1,4,7-triazacyclononane]chlorocopper(II)
perchlorate
top
Crystal data top
[CuCl(C14H21N5)]ClO4 | F(000) = 940 |
Mr = 457.80 | Dx = 1.702 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3169 reflections |
a = 10.336 (1) Å | θ = 2.2–25.1° |
b = 13.428 (1) Å | µ = 1.55 mm−1 |
c = 13.051 (1) Å | T = 293 K |
β = 99.56 (2)° | Block, blue |
V = 1786.2 (3) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 3334 independent reflections |
Radiation source: sealed tube | 2636 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 25.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→12 |
Tmin = 0.696, Tmax = 0.733 | k = −13→16 |
9413 measured reflections | l = −14→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
3334 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.23747 (3) | 0.13246 (2) | 0.06117 (2) | 0.03019 (11) | |
C1 | 0.1721 (3) | 0.2367 (2) | −0.1315 (2) | 0.0371 (7) | |
H1A | 0.1686 | 0.1755 | −0.1713 | 0.044* | |
H1B | 0.1772 | 0.2920 | −0.1785 | 0.044* | |
C2 | 0.0489 (3) | 0.2463 (2) | −0.0828 (2) | 0.0423 (7) | |
H2A | 0.0391 | 0.3148 | −0.0618 | 0.051* | |
H2B | −0.0272 | 0.2290 | −0.1338 | 0.051* | |
C3 | 0.0126 (3) | 0.2279 (2) | 0.1007 (2) | 0.0435 (7) | |
H3A | 0.0031 | 0.1775 | 0.1522 | 0.052* | |
H3B | −0.0719 | 0.2596 | 0.0797 | 0.052* | |
C4 | 0.1122 (3) | 0.3046 (2) | 0.1475 (2) | 0.0417 (7) | |
H4A | 0.1062 | 0.3628 | 0.1030 | 0.050* | |
H4B | 0.0933 | 0.3252 | 0.2148 | 0.050* | |
C5 | 0.3439 (3) | 0.32758 (19) | 0.1218 (2) | 0.0369 (7) | |
H5A | 0.4311 | 0.3004 | 0.1436 | 0.044* | |
H5B | 0.3415 | 0.3936 | 0.1516 | 0.044* | |
C6 | 0.3151 (3) | 0.33456 (18) | 0.0034 (2) | 0.0352 (7) | |
H6A | 0.2394 | 0.3772 | −0.0166 | 0.042* | |
H6B | 0.3892 | 0.3658 | −0.0207 | 0.042* | |
C7 | 0.4076 (2) | 0.19580 (19) | −0.08532 (19) | 0.0319 (6) | |
H7A | 0.4586 | 0.2494 | −0.1087 | 0.038* | |
H7B | 0.3827 | 0.1499 | −0.1426 | 0.038* | |
C8 | 0.4861 (2) | 0.14320 (17) | 0.0048 (2) | 0.0291 (6) | |
C9 | 0.6456 (3) | 0.07650 (18) | 0.1162 (2) | 0.0307 (6) | |
C10 | 0.7629 (3) | 0.04328 (19) | 0.1738 (2) | 0.0387 (7) | |
H10 | 0.8421 | 0.0494 | 0.1494 | 0.046* | |
C11 | 0.7562 (3) | 0.0011 (2) | 0.2684 (2) | 0.0393 (7) | |
H11 | 0.8329 | −0.0215 | 0.3092 | 0.047* | |
C12 | 0.6370 (3) | −0.00916 (19) | 0.3053 (2) | 0.0374 (7) | |
H12 | 0.6367 | −0.0381 | 0.3700 | 0.045* | |
C13 | 0.5205 (3) | 0.02273 (18) | 0.2478 (2) | 0.0333 (6) | |
H13 | 0.4414 | 0.0152 | 0.2721 | 0.040* | |
C14 | 0.5255 (2) | 0.06622 (17) | 0.1528 (2) | 0.0275 (6) | |
Cl1 | 0.19564 (7) | 0.12846 (5) | 0.42264 (5) | 0.03870 (18) | |
Cl2 | 0.17144 (7) | −0.02020 (5) | 0.10957 (6) | 0.04058 (19) | |
N1 | 0.2891 (2) | 0.23624 (14) | −0.04973 (15) | 0.0289 (5) | |
N2 | 0.0552 (2) | 0.18025 (16) | 0.00899 (17) | 0.0375 (6) | |
H2C | 0.0032 | 0.1263 | −0.0096 | 0.045* | |
N3 | 0.2460 (2) | 0.26316 (15) | 0.15981 (16) | 0.0327 (5) | |
H3C | 0.2743 | 0.2460 | 0.2273 | 0.039* | |
N4 | 0.4272 (2) | 0.10768 (14) | 0.07971 (16) | 0.0276 (5) | |
N5 | 0.6146 (2) | 0.12552 (14) | 0.02192 (16) | 0.0321 (5) | |
H5C | 0.6689 | 0.1417 | −0.0185 | 0.039* | |
O1 | 0.0874 (2) | 0.09044 (18) | 0.3521 (2) | 0.0821 (8) | |
O2 | 0.2275 (2) | 0.22619 (14) | 0.38811 (16) | 0.0527 (6) | |
O3 | 0.3077 (2) | 0.06580 (15) | 0.42705 (18) | 0.0605 (6) | |
O4 | 0.1611 (2) | 0.13810 (16) | 0.52315 (16) | 0.0654 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02534 (19) | 0.02599 (18) | 0.0389 (2) | −0.00025 (14) | 0.00432 (14) | 0.00384 (15) |
C1 | 0.0405 (17) | 0.0346 (15) | 0.0329 (16) | 0.0049 (13) | −0.0034 (13) | 0.0030 (13) |
C2 | 0.0339 (17) | 0.0436 (17) | 0.0457 (18) | 0.0061 (13) | −0.0038 (14) | 0.0051 (14) |
C3 | 0.0289 (16) | 0.0483 (18) | 0.055 (2) | 0.0097 (14) | 0.0135 (14) | 0.0102 (15) |
C4 | 0.0462 (19) | 0.0384 (17) | 0.0430 (18) | 0.0112 (14) | 0.0147 (15) | 0.0017 (14) |
C5 | 0.0412 (18) | 0.0279 (14) | 0.0404 (17) | −0.0030 (12) | 0.0031 (14) | −0.0017 (13) |
C6 | 0.0409 (17) | 0.0238 (14) | 0.0413 (17) | −0.0020 (12) | 0.0084 (14) | 0.0004 (12) |
C7 | 0.0326 (16) | 0.0349 (15) | 0.0288 (15) | −0.0007 (12) | 0.0067 (12) | 0.0016 (12) |
C8 | 0.0295 (15) | 0.0260 (14) | 0.0317 (15) | 0.0004 (12) | 0.0046 (12) | −0.0013 (12) |
C9 | 0.0331 (16) | 0.0252 (14) | 0.0332 (16) | −0.0017 (12) | 0.0040 (13) | 0.0011 (12) |
C10 | 0.0272 (16) | 0.0378 (16) | 0.0510 (19) | −0.0004 (13) | 0.0061 (14) | 0.0023 (14) |
C11 | 0.0363 (17) | 0.0347 (16) | 0.0425 (18) | 0.0038 (13) | −0.0070 (14) | 0.0005 (14) |
C12 | 0.0472 (19) | 0.0306 (15) | 0.0320 (16) | 0.0009 (13) | −0.0002 (14) | 0.0048 (12) |
C13 | 0.0352 (16) | 0.0289 (14) | 0.0363 (16) | −0.0009 (12) | 0.0072 (13) | 0.0010 (12) |
C14 | 0.0290 (15) | 0.0205 (13) | 0.0329 (16) | −0.0006 (11) | 0.0051 (12) | 0.0003 (11) |
Cl1 | 0.0373 (4) | 0.0345 (4) | 0.0447 (4) | 0.0033 (3) | 0.0078 (3) | 0.0027 (3) |
Cl2 | 0.0387 (4) | 0.0314 (4) | 0.0523 (5) | −0.0053 (3) | 0.0092 (3) | 0.0065 (3) |
N1 | 0.0284 (12) | 0.0263 (11) | 0.0314 (12) | 0.0012 (9) | 0.0036 (10) | 0.0046 (10) |
N2 | 0.0262 (13) | 0.0359 (13) | 0.0489 (15) | −0.0019 (10) | 0.0014 (11) | 0.0042 (11) |
N3 | 0.0373 (14) | 0.0304 (12) | 0.0302 (13) | 0.0007 (10) | 0.0052 (10) | 0.0006 (10) |
N4 | 0.0274 (12) | 0.0256 (11) | 0.0302 (12) | −0.0015 (9) | 0.0065 (10) | 0.0025 (9) |
N5 | 0.0283 (13) | 0.0351 (13) | 0.0351 (13) | −0.0005 (10) | 0.0118 (10) | 0.0053 (10) |
O1 | 0.0628 (17) | 0.0709 (16) | 0.103 (2) | −0.0015 (13) | −0.0152 (15) | −0.0297 (15) |
O2 | 0.0663 (15) | 0.0397 (12) | 0.0589 (14) | 0.0049 (10) | 0.0302 (12) | 0.0092 (10) |
O3 | 0.0528 (14) | 0.0521 (13) | 0.0802 (17) | 0.0189 (11) | 0.0221 (13) | 0.0082 (12) |
O4 | 0.0733 (17) | 0.0779 (17) | 0.0516 (15) | 0.0238 (13) | 0.0299 (13) | 0.0254 (12) |
Geometric parameters (Å, º) top
Cu1—N4 | 1.964 (2) | C7—N1 | 1.483 (3) |
Cu1—N2 | 2.000 (2) | C7—C8 | 1.491 (3) |
Cu1—N1 | 2.1398 (19) | C7—H7A | 0.9700 |
Cu1—N3 | 2.170 (2) | C7—H7B | 0.9700 |
Cu1—Cl2 | 2.2827 (7) | C8—N4 | 1.323 (3) |
C1—N1 | 1.475 (3) | C8—N5 | 1.331 (3) |
C1—C2 | 1.520 (4) | C9—C10 | 1.390 (4) |
C1—H1A | 0.9700 | C9—N5 | 1.385 (3) |
C1—H1B | 0.9700 | C9—C14 | 1.408 (3) |
C2—N2 | 1.483 (3) | C10—C11 | 1.370 (4) |
C2—H2A | 0.9700 | C10—H10 | 0.9300 |
C2—H2B | 0.9700 | C11—C12 | 1.402 (4) |
C3—N2 | 1.486 (3) | C11—H11 | 0.9300 |
C3—C4 | 1.512 (4) | C12—C13 | 1.378 (4) |
C3—H3A | 0.9700 | C12—H12 | 0.9300 |
C3—H3B | 0.9700 | C13—C14 | 1.379 (3) |
C4—N3 | 1.475 (3) | C13—H13 | 0.9300 |
C4—H4A | 0.9700 | C14—N4 | 1.389 (3) |
C4—H4B | 0.9700 | Cl1—O4 | 1.422 (2) |
C5—N3 | 1.479 (3) | Cl1—O1 | 1.420 (2) |
C5—C6 | 1.527 (4) | Cl1—O3 | 1.425 (2) |
C5—H5A | 0.9700 | Cl1—O2 | 1.4433 (19) |
C5—H5B | 0.9700 | N2—H2C | 0.9100 |
C6—N1 | 1.495 (3) | N3—H3C | 0.9100 |
C6—H6A | 0.9700 | N5—H5C | 0.8600 |
C6—H6B | 0.9700 | | |
| | | |
N4—Cu1—N2 | 164.01 (9) | N4—C8—N5 | 112.3 (2) |
N4—Cu1—N1 | 80.64 (8) | N4—C8—C7 | 119.8 (2) |
N2—Cu1—N1 | 83.55 (8) | N5—C8—C7 | 127.9 (2) |
N4—Cu1—N3 | 97.04 (8) | C10—C9—N5 | 133.2 (2) |
N2—Cu1—N3 | 83.43 (9) | C10—C9—C14 | 121.6 (2) |
N1—Cu1—N3 | 83.37 (8) | N5—C9—C14 | 105.2 (2) |
N4—Cu1—Cl2 | 98.75 (6) | C11—C10—C9 | 116.7 (3) |
N2—Cu1—Cl2 | 94.26 (7) | C11—C10—H10 | 121.6 |
N1—Cu1—Cl2 | 153.09 (6) | C9—C10—H10 | 121.6 |
N3—Cu1—Cl2 | 123.14 (6) | C10—C11—C12 | 122.0 (3) |
N1—C1—C2 | 110.0 (2) | C10—C11—H11 | 119.0 |
N1—C1—H1A | 109.7 | C12—C11—H11 | 119.0 |
C2—C1—H1A | 109.7 | C13—C12—C11 | 121.4 (3) |
N1—C1—H1B | 109.7 | C13—C12—H12 | 119.3 |
C2—C1—H1B | 109.7 | C11—C12—H12 | 119.3 |
H1A—C1—H1B | 108.2 | C12—C13—C14 | 117.5 (3) |
N2—C2—C1 | 111.1 (2) | C12—C13—H13 | 121.3 |
N2—C2—H2A | 109.4 | C14—C13—H13 | 121.3 |
C1—C2—H2A | 109.4 | C13—C14—N4 | 130.9 (2) |
N2—C2—H2B | 109.4 | C13—C14—C9 | 120.9 (2) |
C1—C2—H2B | 109.4 | N4—C14—C9 | 108.2 (2) |
H2A—C2—H2B | 108.0 | O4—Cl1—O1 | 109.83 (16) |
N2—C3—C4 | 110.3 (2) | O4—Cl1—O3 | 110.08 (14) |
N2—C3—H3A | 109.6 | O1—Cl1—O3 | 111.18 (15) |
C4—C3—H3A | 109.6 | O4—Cl1—O2 | 108.10 (13) |
N2—C3—H3B | 109.6 | O1—Cl1—O2 | 108.70 (15) |
C4—C3—H3B | 109.6 | O3—Cl1—O2 | 108.88 (13) |
H3A—C3—H3B | 108.1 | C1—N1—C7 | 113.32 (19) |
N3—C4—C3 | 110.5 (2) | C1—N1—C6 | 113.2 (2) |
N3—C4—H4A | 109.6 | C7—N1—C6 | 112.0 (2) |
C3—C4—H4A | 109.6 | C1—N1—Cu1 | 103.02 (15) |
N3—C4—H4B | 109.6 | C7—N1—Cu1 | 106.57 (14) |
C3—C4—H4B | 109.6 | C6—N1—Cu1 | 107.90 (15) |
H4A—C4—H4B | 108.1 | C2—N2—C3 | 114.4 (2) |
N3—C5—C6 | 110.3 (2) | C2—N2—Cu1 | 112.28 (16) |
N3—C5—H5A | 109.6 | C3—N2—Cu1 | 104.60 (16) |
C6—C5—H5A | 109.6 | C2—N2—H2C | 108.4 |
N3—C5—H5B | 109.6 | C3—N2—H2C | 108.4 |
C6—C5—H5B | 109.6 | Cu1—N2—H2C | 108.4 |
H5A—C5—H5B | 108.1 | C4—N3—C5 | 115.1 (2) |
N1—C6—C5 | 113.9 (2) | C4—N3—Cu1 | 107.21 (16) |
N1—C6—H6A | 108.8 | C5—N3—Cu1 | 103.69 (14) |
C5—C6—H6A | 108.8 | C4—N3—H3C | 110.2 |
N1—C6—H6B | 108.8 | C5—N3—H3C | 110.2 |
C5—C6—H6B | 108.8 | Cu1—N3—H3C | 110.2 |
H6A—C6—H6B | 107.7 | C8—N4—C14 | 106.2 (2) |
N1—C7—C8 | 107.21 (19) | C8—N4—Cu1 | 114.84 (17) |
N1—C7—H7A | 110.3 | C14—N4—Cu1 | 138.90 (17) |
C8—C7—H7A | 110.3 | C8—N5—C9 | 108.1 (2) |
N1—C7—H7B | 110.3 | C8—N5—H5C | 126.0 |
C8—C7—H7B | 110.3 | C9—N5—H5C | 126.0 |
H7A—C7—H7B | 108.5 | | |
| | | |
N1—C1—C2—N2 | −44.1 (3) | N4—Cu1—N2—C2 | −0.7 (4) |
N2—C3—C4—N3 | −47.5 (3) | N1—Cu1—N2—C2 | 7.89 (17) |
N3—C5—C6—N1 | −47.3 (3) | N3—Cu1—N2—C2 | 91.92 (18) |
N1—C7—C8—N4 | 25.0 (3) | Cl2—Cu1—N2—C2 | −145.17 (17) |
N1—C7—C8—N5 | −155.1 (2) | N4—Cu1—N2—C3 | −125.4 (3) |
N5—C9—C10—C11 | 176.9 (3) | N1—Cu1—N2—C3 | −116.76 (17) |
C14—C9—C10—C11 | −0.7 (4) | N3—Cu1—N2—C3 | −32.74 (16) |
C9—C10—C11—C12 | 0.5 (4) | Cl2—Cu1—N2—C3 | 90.17 (16) |
C10—C11—C12—C13 | 0.2 (4) | C3—C4—N3—C5 | 132.4 (2) |
C11—C12—C13—C14 | −0.7 (4) | C3—C4—N3—Cu1 | 17.7 (3) |
C12—C13—C14—N4 | −177.9 (2) | C6—C5—N3—C4 | −69.2 (3) |
C12—C13—C14—C9 | 0.6 (4) | C6—C5—N3—Cu1 | 47.6 (2) |
C10—C9—C14—C13 | 0.1 (4) | N4—Cu1—N3—C4 | 172.69 (16) |
N5—C9—C14—C13 | −178.0 (2) | N2—Cu1—N3—C4 | 8.78 (16) |
C10—C9—C14—N4 | 178.9 (2) | N1—Cu1—N3—C4 | 93.02 (16) |
N5—C9—C14—N4 | 0.8 (3) | Cl2—Cu1—N3—C4 | −82.02 (16) |
C2—C1—N1—C7 | 161.7 (2) | N4—Cu1—N3—C5 | 50.46 (16) |
C2—C1—N1—C6 | −69.3 (3) | N2—Cu1—N3—C5 | −113.44 (16) |
C2—C1—N1—Cu1 | 47.0 (2) | N1—Cu1—N3—C5 | −29.20 (16) |
C8—C7—N1—C1 | −146.3 (2) | Cl2—Cu1—N3—C5 | 155.75 (13) |
C8—C7—N1—C6 | 84.1 (2) | N5—C8—N4—C14 | 1.9 (3) |
C8—C7—N1—Cu1 | −33.7 (2) | C7—C8—N4—C14 | −178.3 (2) |
C5—C6—N1—C1 | 132.9 (2) | N5—C8—N4—Cu1 | 179.17 (16) |
C5—C6—N1—C7 | −97.5 (3) | C7—C8—N4—Cu1 | −0.9 (3) |
C5—C6—N1—Cu1 | 19.5 (3) | C13—C14—N4—C8 | 177.0 (3) |
N4—Cu1—N1—C1 | 147.32 (16) | C9—C14—N4—C8 | −1.6 (3) |
N2—Cu1—N1—C1 | −30.29 (15) | C13—C14—N4—Cu1 | 0.7 (4) |
N3—Cu1—N1—C1 | −114.39 (16) | C9—C14—N4—Cu1 | −177.86 (18) |
Cl2—Cu1—N1—C1 | 56.4 (2) | N2—Cu1—N4—C8 | −6.7 (4) |
N4—Cu1—N1—C7 | 27.79 (15) | N1—Cu1—N4—C8 | −15.41 (17) |
N2—Cu1—N1—C7 | −149.81 (16) | N3—Cu1—N4—C8 | −97.46 (18) |
N3—Cu1—N1—C7 | 126.09 (16) | Cl2—Cu1—N4—C8 | 137.34 (16) |
Cl2—Cu1—N1—C7 | −63.1 (2) | N2—Cu1—N4—C14 | 169.3 (3) |
N4—Cu1—N1—C6 | −92.67 (16) | N1—Cu1—N4—C14 | 160.7 (3) |
N2—Cu1—N1—C6 | 89.72 (16) | N3—Cu1—N4—C14 | 78.6 (2) |
N3—Cu1—N1—C6 | 5.62 (16) | Cl2—Cu1—N4—C14 | −46.6 (2) |
Cl2—Cu1—N1—C6 | 176.42 (12) | N4—C8—N5—C9 | −1.4 (3) |
C1—C2—N2—C3 | 135.4 (2) | C7—C8—N5—C9 | 178.7 (2) |
C1—C2—N2—Cu1 | 16.4 (3) | C10—C9—N5—C8 | −177.5 (3) |
C4—C3—N2—C2 | −70.3 (3) | C14—C9—N5—C8 | 0.3 (3) |
C4—C3—N2—Cu1 | 53.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···Cl2i | 0.91 | 2.49 | 3.361 (2) | 160 |
N3—H3C···O2 | 0.91 | 2.25 | 3.058 (3) | 148 |
N5—H5C···O2ii | 0.86 | 2.29 | 3.009 (3) | 141 |
N5—H5C···Cl2iii | 0.86 | 2.73 | 3.331 (2) | 128 |
Symmetry codes: (i) −x, −y, −z; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z. |