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In the title compound, [CuCl(C6H4N2)(C6H15N3)]ClO4, the central copper ion is coordinated by three N atoms from 1,4,7-triaza­cyclo­nonane, one N atom from the cyano­pyridine and one Cl atom, forming a square-pyramidal coordination geometry (τ = 0.31). The crystal packing is stabilized by inter­molecular N—H...O and N—H...Cl hydro­gen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012870/cv6493sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012870/cv6493Isup2.hkl
Contains datablock I

CCDC reference: 244890

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.033
  • wR factor = 0.086
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C12 ... 1.45 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9 N4 -CU1 -N2 -C2 -3.60 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N4 -CU1 -N2 -C3 -128.50 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 25 N2 -CU1 -N4 -C7 -30.50 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 29 N2 -CU1 -N4 -C11 148.80 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 58 C10 -C9 -C12 -N5 -48.00 16.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 59 C8 -C9 -C12 -N5 130.00 16.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 284 _chemical_formula_iupac '[Cu Cl (C6 H4 N2) (C6 H15 N3)] Cl O4~' If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Chloro(pyridine-4-carbonitrile-κN1)(1,4,7-triazacyclononane- κ3N,N',N'')copper(II) perchlorate top
Crystal data top
[CuCl(C6H4N2)(C6H15N3)]ClO4Z = 2
Mr = 431.77F(000) = 442
Triclinic, P1Dx = 1.682 Mg m3
a = 7.656 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.707 (5) ÅCell parameters from 819 reflections
c = 10.933 (5) Åθ = 3.3–26.3°
α = 73.065 (6)°µ = 1.62 mm1
β = 84.573 (7)°T = 293 K
γ = 86.058 (7)°Block, blue
V = 852.7 (7) Å30.24 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3453 independent reflections
Radiation source: fine-focus sealed tube2822 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.621, Tmax = 0.771k = 1311
4946 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.5194P]
where P = (Fo2 + 2Fc2)/3
3453 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.35 e Å3
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
Cu10.06081 (4)0.74897 (3)0.12784 (3)0.03029 (11)
N10.2074 (3)0.6065 (2)0.2580 (2)0.0353 (5)
H10.13420.56380.32550.042*
N20.1905 (3)0.6674 (2)0.0011 (2)0.0332 (5)
H20.11990.67510.06560.040*
N30.3021 (3)0.8568 (2)0.0996 (2)0.0343 (5)
H30.27790.93800.10930.041*
N40.0708 (3)0.8120 (2)0.2706 (2)0.0337 (5)
N50.3874 (5)0.9583 (4)0.6672 (3)0.0767 (10)
Cl10.15771 (9)0.82263 (8)0.00475 (7)0.04274 (19)
C10.2931 (4)0.5111 (3)0.1936 (3)0.0425 (7)
H1A0.27760.42300.24900.051*
H1B0.41800.52510.17750.051*
C20.2141 (4)0.5267 (3)0.0685 (3)0.0437 (7)
H2A0.29060.48330.01610.052*
H2B0.10140.48630.08510.052*
C30.3568 (4)0.7328 (3)0.0578 (3)0.0408 (7)
H3A0.36890.74310.14930.049*
H3B0.45560.67830.02000.049*
C40.3600 (4)0.8652 (3)0.0350 (3)0.0399 (7)
H4A0.47810.89670.05470.048*
H4B0.28310.92690.09140.048*
C50.4242 (4)0.7815 (3)0.1934 (3)0.0414 (7)
H5A0.48170.84100.22710.050*
H5B0.51410.73730.15050.050*
C60.3310 (4)0.6813 (3)0.3035 (3)0.0436 (7)
H6A0.41750.62100.35160.052*
H6B0.26660.72540.36080.052*
C70.1823 (4)0.7341 (3)0.3556 (3)0.0408 (7)
H70.20160.65300.34540.049*
C80.2698 (4)0.7685 (3)0.4575 (3)0.0419 (7)
H80.34620.71170.51520.050*
C90.2422 (4)0.8890 (3)0.4723 (3)0.0372 (6)
C100.1312 (4)0.9715 (3)0.3831 (3)0.0452 (7)
H100.11271.05400.38990.054*
C110.0485 (4)0.9299 (3)0.2842 (3)0.0423 (7)
H110.02600.98600.22410.051*
C120.3254 (5)0.9274 (4)0.5812 (3)0.0518 (8)
Cl20.17806 (10)0.62979 (8)0.66298 (7)0.04503 (19)
O10.0566 (4)0.7081 (3)0.7227 (3)0.0765 (8)
O20.0889 (3)0.5869 (2)0.5737 (2)0.0579 (6)
O30.2285 (5)0.5188 (3)0.7651 (3)0.0846 (9)
O40.3192 (5)0.7065 (4)0.6023 (3)0.1115 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02201 (17)0.0419 (2)0.02978 (18)0.00410 (13)0.00026 (12)0.01666 (14)
N10.0305 (12)0.0454 (14)0.0274 (11)0.0001 (10)0.0020 (9)0.0081 (10)
N20.0267 (11)0.0462 (14)0.0308 (12)0.0022 (10)0.0021 (9)0.0183 (10)
N30.0299 (12)0.0394 (13)0.0361 (12)0.0039 (10)0.0037 (9)0.0159 (10)
N40.0262 (11)0.0453 (14)0.0325 (12)0.0035 (10)0.0003 (9)0.0176 (10)
N50.086 (2)0.097 (3)0.0525 (19)0.012 (2)0.0143 (17)0.0402 (19)
Cl10.0297 (3)0.0569 (5)0.0382 (4)0.0098 (3)0.0050 (3)0.0102 (3)
C10.0395 (16)0.0390 (16)0.0461 (17)0.0063 (13)0.0034 (13)0.0096 (13)
C20.0421 (17)0.0441 (17)0.0496 (18)0.0034 (13)0.0000 (13)0.0233 (14)
C30.0347 (15)0.0578 (19)0.0302 (14)0.0011 (13)0.0068 (11)0.0170 (13)
C40.0349 (15)0.0483 (17)0.0328 (15)0.0037 (13)0.0051 (12)0.0080 (13)
C50.0288 (14)0.062 (2)0.0407 (16)0.0065 (13)0.0031 (12)0.0247 (15)
C60.0397 (16)0.061 (2)0.0306 (15)0.0031 (14)0.0064 (12)0.0136 (14)
C70.0338 (15)0.0427 (17)0.0506 (18)0.0021 (12)0.0030 (13)0.0228 (14)
C80.0333 (15)0.0496 (18)0.0402 (16)0.0023 (13)0.0089 (12)0.0126 (14)
C90.0347 (15)0.0484 (17)0.0298 (14)0.0083 (12)0.0005 (11)0.0163 (13)
C100.0554 (19)0.0386 (17)0.0446 (17)0.0000 (14)0.0061 (14)0.0202 (14)
C110.0444 (17)0.0409 (17)0.0383 (16)0.0021 (13)0.0095 (13)0.0102 (13)
C120.0510 (19)0.065 (2)0.0435 (18)0.0055 (16)0.0030 (15)0.0254 (17)
Cl20.0499 (4)0.0505 (5)0.0384 (4)0.0126 (3)0.0011 (3)0.0170 (3)
O10.090 (2)0.0704 (18)0.0738 (18)0.0082 (15)0.0061 (15)0.0345 (15)
O20.0679 (16)0.0674 (16)0.0430 (12)0.0195 (13)0.0116 (11)0.0170 (12)
O30.122 (3)0.0716 (19)0.0650 (17)0.0219 (17)0.0403 (17)0.0228 (15)
O40.103 (3)0.171 (4)0.083 (2)0.089 (3)0.0417 (19)0.068 (2)
Geometric parameters (Å, º) top
Cu1—N22.017 (2)C3—H3A0.9700
Cu1—N42.032 (2)C3—H3B0.9700
Cu1—N12.101 (2)C4—H4A0.9700
Cu1—N32.195 (2)C4—H4B0.9700
Cu1—Cl12.2658 (10)C5—C61.517 (4)
N1—C61.486 (4)C5—H5A0.9700
N1—C11.486 (4)C5—H5B0.9700
N1—H10.9100C6—H6A0.9700
N2—C21.484 (4)C6—H6B0.9700
N2—C31.489 (4)C7—C81.374 (4)
N2—H20.9100C7—H70.9300
N3—C51.474 (4)C8—C91.378 (4)
N3—C41.475 (3)C8—H80.9300
N3—H30.9100C9—C101.377 (4)
N4—C71.336 (4)C9—C121.449 (4)
N4—C111.338 (4)C10—C111.372 (4)
N5—C121.137 (4)C10—H100.9300
C1—C21.508 (4)C11—H110.9300
C1—H1A0.9700Cl2—O41.397 (3)
C1—H1B0.9700Cl2—O31.433 (3)
C2—H2A0.9700Cl2—O21.435 (2)
C2—H2B0.9700Cl2—O11.446 (3)
C3—C41.512 (4)
N2—Cu1—N4174.01 (9)C4—C3—H3A109.4
N2—Cu1—N182.99 (9)N2—C3—H3B109.4
N4—Cu1—N192.22 (9)C4—C3—H3B109.4
N2—Cu1—N382.77 (9)H3A—C3—H3B108.0
N4—Cu1—N3100.23 (9)N3—C4—C3110.5 (2)
N1—Cu1—N382.53 (9)N3—C4—H4A109.6
N2—Cu1—Cl190.25 (7)C3—C4—H4A109.6
N4—Cu1—Cl192.63 (7)N3—C4—H4B109.6
N1—Cu1—Cl1155.03 (7)C3—C4—H4B109.6
N3—Cu1—Cl1120.56 (7)H4A—C4—H4B108.1
C6—N1—C1114.6 (2)N3—C5—C6112.0 (2)
C6—N1—Cu1104.89 (18)N3—C5—H5A109.2
C1—N1—Cu1109.61 (17)C6—C5—H5A109.2
C6—N1—H1109.2N3—C5—H5B109.2
C1—N1—H1109.2C6—C5—H5B109.2
Cu1—N1—H1109.2H5A—C5—H5B107.9
C2—N2—C3114.3 (2)N1—C6—C5112.0 (2)
C2—N2—Cu1105.13 (16)N1—C6—H6A109.2
C3—N2—Cu1112.33 (17)C5—C6—H6A109.2
C2—N2—H2108.3N1—C6—H6B109.2
C3—N2—H2108.3C5—C6—H6B109.2
Cu1—N2—H2108.3H6A—C6—H6B107.9
C5—N3—C4114.5 (2)N4—C7—C8122.9 (3)
C5—N3—Cu1108.40 (17)N4—C7—H7118.5
C4—N3—Cu1101.57 (17)C8—C7—H7118.5
C5—N3—H3110.7C7—C8—C9118.6 (3)
C4—N3—H3110.7C7—C8—H8120.7
Cu1—N3—H3110.7C9—C8—H8120.7
C7—N4—C11117.8 (2)C10—C9—C8118.9 (3)
C7—N4—Cu1120.00 (19)C10—C9—C12120.4 (3)
C11—N4—Cu1122.15 (19)C8—C9—C12120.7 (3)
N1—C1—C2110.2 (2)C11—C10—C9119.0 (3)
N1—C1—H1A109.6C11—C10—H10120.5
C2—C1—H1A109.6C9—C10—H10120.5
N1—C1—H1B109.6N4—C11—C10122.7 (3)
C2—C1—H1B109.6N4—C11—H11118.7
H1A—C1—H1B108.1C10—C11—H11118.7
N2—C2—C1110.0 (2)N5—C12—C9178.5 (4)
N2—C2—H2A109.7O4—Cl2—O3112.9 (2)
C1—C2—H2A109.7O4—Cl2—O2111.72 (17)
N2—C2—H2B109.7O3—Cl2—O2109.39 (17)
C1—C2—H2B109.7O4—Cl2—O1107.9 (2)
H2A—C2—H2B108.2O3—Cl2—O1105.57 (18)
N2—C3—C4111.3 (2)O2—Cl2—O1109.10 (17)
N2—C3—H3A109.4
N2—Cu1—N1—C6112.30 (17)N3—Cu1—N4—C1129.2 (2)
N4—Cu1—N1—C671.31 (17)Cl1—Cu1—N4—C1192.5 (2)
N3—Cu1—N1—C628.72 (16)C6—N1—C1—C2131.4 (3)
Cl1—Cu1—N1—C6172.38 (13)Cu1—N1—C1—C213.8 (3)
N2—Cu1—N1—C111.26 (18)C3—N2—C2—C172.6 (3)
N4—Cu1—N1—C1165.13 (19)Cu1—N2—C2—C151.1 (3)
N3—Cu1—N1—C194.84 (19)N1—C1—C2—N243.1 (3)
Cl1—Cu1—N1—C164.1 (2)C2—N2—C3—C4136.5 (3)
N4—Cu1—N2—C23.6 (9)Cu1—N2—C3—C416.8 (3)
N1—Cu1—N2—C233.47 (18)C5—N3—C4—C368.1 (3)
N3—Cu1—N2—C2116.79 (18)Cu1—N3—C4—C348.5 (2)
Cl1—Cu1—N2—C2122.42 (17)N2—C3—C4—N346.2 (3)
N4—Cu1—N2—C3128.5 (8)C4—N3—C5—C6130.8 (3)
N1—Cu1—N2—C391.47 (19)Cu1—N3—C5—C618.2 (3)
N3—Cu1—N2—C38.15 (18)C1—N1—C6—C572.0 (3)
Cl1—Cu1—N2—C3112.64 (18)Cu1—N1—C6—C548.3 (3)
N2—Cu1—N3—C589.98 (18)N3—C5—C6—N145.8 (3)
N4—Cu1—N3—C584.77 (18)C11—N4—C7—C82.0 (4)
N1—Cu1—N3—C56.14 (17)Cu1—N4—C7—C8177.2 (2)
Cl1—Cu1—N3—C5175.98 (14)N4—C7—C8—C90.3 (5)
N2—Cu1—N3—C430.91 (17)C7—C8—C9—C101.5 (4)
N4—Cu1—N3—C4154.34 (17)C7—C8—C9—C12177.3 (3)
N1—Cu1—N3—C4114.75 (18)C8—C9—C10—C111.6 (5)
Cl1—Cu1—N3—C455.09 (18)C12—C9—C10—C11177.2 (3)
N2—Cu1—N4—C730.5 (10)C7—N4—C11—C101.9 (4)
N1—Cu1—N4—C767.2 (2)Cu1—N4—C11—C10177.3 (2)
N3—Cu1—N4—C7150.0 (2)C9—C10—C11—N40.2 (5)
Cl1—Cu1—N4—C788.3 (2)C10—C9—C12—N548 (16)
N2—Cu1—N4—C11148.8 (8)C8—C9—C12—N5130 (16)
N1—Cu1—N4—C11112.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.912.393.234 (3)154
N2—H2···O1ii0.912.333.181 (4)156
N3—H3···Cl1iii0.912.633.420 (3)146
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z1; (iii) x, y+2, z.
 

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