[1-(Benzimidazol-2-yl­methyl)-1,4,7-tri­aza­cyclo­nonane]­chloro­copper(II) perchlorate

In the title complex, [Cu^IICl(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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

[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) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···Cl2^i	0.91	2.49	3.361 (2)	160
N3—H3C···O2	0.91	2.25	3.058 (3)	148
N5—H5C···O2^ii	0.86	2.29	3.009 (3)	141
N5—H5C···Cl2^iii	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.