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(Dicyanamido-κN1)bis­(5,5′-dimethyl-2,2′-bi­pyridine-κ2N,N′)copper(II) tetra­fluoro­borate, [Cu{N(CN)2}(C12H12N2)2]BF4, (I), and (dicyanamido-κN1)bis­(5,5′-dimethyl-2,2′-bi­pyridine-κ2N,N′)copper(II) perchlorate, [Cu{N(CN)2}(C12H12N2)2]ClO4, (II), are isomorphous and consist of [Cu{N(CN)2}(mbpy)2]+ cations (mbpy is 5,5′-dimethyl-2,2′-bi­pyridine) and BF4 or ClO4 anions, respectively. The CuII cations in both structures are five-coordinated in distorted trigonal bipy­rami­dal environments by four N atoms of two mbpy ligands and one N atom of the dicyanamide anion, which is coordinated in a monodentate manner in the equatorial plane, with Cu—N distances of 1.980 (3) and 1.977 (2) Å in (I) and (II), respectively. The two axial Cu—Nmbpy bonds have very similar values [1.986 (1) Å on average] and are shorter than the other two equatorial Cu—Nmbpy bonds. These have different values in the individual compounds but nevertheless form two pairs of similar bonds in (I) and (II) [2.066 (8) and 2.112 (2) Å, respectively, on average]. Besides the ionic forces in both structures, the structures are stabilized by C—H...N and C—H...X hydrogen bonds (X = F and O, respectively), and by π–π inter­actions between the pyridine rings of neighbouring mbpy mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113027091/fg3305sup1.cif
Contains datablocks cumbdf__I, cumbdc__II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027091/fg3305cumbdf__Isup2.hkl
Contains datablock cumbdf__I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027091/fg3305cumbdc__IIsup3.hkl
Contains datablock cumbdc__II

CCDC references: 964425; 964426

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(cumbdf__I) (Dicyanamido-κN1)bis(5,5'-dimethyl-2,2'-bipyridine-κ2N,N')copper(II) tetrafluoroborate top
Crystal data top
[Cu(c2N3)(C12H12N2)2]BF4F(000) = 1196
Mr = 584.87Dx = 1.488 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10476 reflections
a = 13.6714 (8) Åθ = 2.6–26.5°
b = 17.0453 (17) ŵ = 0.90 mm1
c = 11.2195 (11) ÅT = 120 K
β = 93.361 (7)°Prism, dark green-blue
V = 2610.0 (4) Å30.62 × 0.17 × 0.09 mm
Z = 4
Data collection top
Oxford MODEL?? CCD area-detector
diffractometer
5118 independent reflections
Radiation source: Enhance (Mo) X-ray Source3476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 8.3438 pixels mm-1θmax = 26.0°, θmin = 2.7°
Rotation method data acquisition using ω scansh = 1616
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 2121
Tmin = 0.902, Tmax = 1.000l = 1313
31369 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0704P)2]
where P = (Fo2 + 2Fc2)/3
5118 reflections(Δ/σ)max = 0.001
356 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction, 2007. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cu10.75447 (2)0.50007 (2)0.47088 (3)0.01707 (13)
N100.65590 (17)0.49331 (13)0.3342 (2)0.0175 (5)
N200.64331 (17)0.57242 (14)0.5336 (2)0.0174 (5)
N300.85829 (17)0.50938 (13)0.6016 (2)0.0166 (5)
N400.83855 (17)0.58789 (14)0.4005 (2)0.0177 (5)
C110.5709 (2)0.53307 (18)0.3440 (3)0.0191 (7)
C120.6662 (2)0.44677 (17)0.2394 (3)0.0238 (7)
H120.72650.41980.23360.029*
C130.5933 (2)0.43577 (18)0.1490 (3)0.0255 (7)
C140.5070 (2)0.4768 (2)0.1597 (3)0.0280 (8)
H140.45510.47140.10020.034*
C150.4957 (2)0.52530 (19)0.2559 (3)0.0250 (7)
H150.43630.55360.26210.030*
C160.6100 (3)0.3815 (2)0.0468 (3)0.0381 (9)
H16A0.54830.37400.00100.057*
H16B0.63340.33070.07800.057*
H16C0.65900.40420.00320.057*
C210.5669 (2)0.58142 (17)0.4524 (3)0.0183 (7)
C220.6471 (2)0.61666 (17)0.6327 (3)0.0210 (7)
H220.70050.60940.68970.025*
C230.5765 (2)0.67266 (18)0.6561 (3)0.0239 (7)
C240.4978 (2)0.67950 (19)0.5728 (3)0.0262 (7)
H240.44700.71600.58610.031*
C250.4923 (2)0.63415 (18)0.4711 (3)0.0239 (7)
H250.43820.63900.41450.029*
C260.5858 (3)0.7232 (2)0.7657 (3)0.0372 (9)
H26A0.61280.77440.74520.056*
H26B0.62960.69780.82630.056*
H26C0.52110.73050.79730.056*
C310.9303 (2)0.56246 (16)0.5837 (3)0.0174 (6)
C320.8636 (2)0.46468 (18)0.6991 (3)0.0198 (7)
H320.81220.42830.71000.024*
C330.9400 (2)0.46838 (19)0.7857 (3)0.0213 (7)
C341.0138 (2)0.52262 (18)0.7676 (3)0.0224 (7)
H341.06790.52740.82430.027*
C351.0083 (2)0.56964 (18)0.6669 (3)0.0221 (7)
H351.05830.60700.65490.027*
C360.9422 (2)0.41545 (18)0.8932 (3)0.0268 (8)
H36A0.89010.43080.94490.040*
H36B1.00590.42010.93750.040*
H36C0.93210.36100.86730.040*
C410.9166 (2)0.60861 (17)0.4725 (3)0.0188 (7)
C420.8174 (2)0.62878 (17)0.3008 (3)0.0204 (7)
H420.76210.61330.25100.024*
C430.8715 (2)0.69235 (18)0.2660 (3)0.0247 (7)
C440.9534 (2)0.71257 (18)0.3394 (3)0.0273 (8)
H440.99340.75540.31850.033*
C450.9767 (2)0.67043 (18)0.4427 (3)0.0235 (7)
H451.03300.68360.49240.028*
C460.8429 (3)0.73715 (19)0.1550 (3)0.0309 (8)
H46A0.88870.72520.09360.046*
H46B0.84460.79350.17230.046*
H46C0.77640.72210.12620.046*
C10.7693 (2)0.3224 (2)0.4426 (3)0.0319 (8)
N10.76171 (18)0.38416 (16)0.4790 (2)0.0278 (6)
C20.7297 (3)0.2187 (2)0.3215 (4)0.0410 (10)
N20.6823 (2)0.18364 (19)0.2513 (3)0.0463 (9)
N30.7878 (3)0.2528 (2)0.4060 (4)0.0772 (15)
B11.2455 (3)0.4243 (3)1.0386 (4)0.0318 (9)
F11.19149 (18)0.37021 (14)1.0997 (2)0.0597 (7)
F21.32476 (14)0.38772 (12)0.98906 (19)0.0431 (5)
F31.27936 (14)0.48226 (12)1.11884 (18)0.0384 (5)
F41.18741 (15)0.45822 (14)0.94757 (19)0.0498 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0175 (2)0.0165 (2)0.0167 (2)0.00030 (15)0.00310 (14)0.00015 (15)
N100.0167 (13)0.0182 (13)0.0176 (13)0.0008 (11)0.0000 (10)0.0002 (11)
N200.0171 (13)0.0176 (13)0.0174 (13)0.0006 (10)0.0006 (11)0.0035 (10)
N300.0148 (12)0.0165 (13)0.0184 (13)0.0009 (10)0.0003 (10)0.0020 (10)
N400.0174 (13)0.0186 (13)0.0172 (13)0.0013 (10)0.0022 (11)0.0006 (10)
C110.0193 (16)0.0183 (15)0.0198 (16)0.0033 (13)0.0018 (13)0.0063 (13)
C120.0248 (17)0.0221 (17)0.0244 (17)0.0013 (13)0.0002 (14)0.0028 (14)
C130.0325 (19)0.0272 (18)0.0163 (16)0.0077 (15)0.0022 (14)0.0027 (13)
C140.0226 (18)0.041 (2)0.0193 (17)0.0102 (15)0.0073 (14)0.0031 (15)
C150.0200 (17)0.0319 (18)0.0225 (17)0.0036 (14)0.0036 (14)0.0062 (14)
C160.055 (2)0.038 (2)0.0209 (18)0.0046 (18)0.0053 (17)0.0048 (16)
C210.0167 (15)0.0213 (16)0.0173 (16)0.0024 (12)0.0027 (13)0.0032 (12)
C220.0204 (16)0.0235 (17)0.0192 (16)0.0028 (13)0.0009 (13)0.0009 (13)
C230.0277 (18)0.0189 (16)0.0258 (18)0.0013 (14)0.0076 (14)0.0001 (13)
C240.0237 (17)0.0216 (17)0.034 (2)0.0045 (14)0.0066 (15)0.0037 (15)
C250.0170 (16)0.0225 (17)0.032 (2)0.0008 (13)0.0021 (14)0.0090 (14)
C260.044 (2)0.033 (2)0.035 (2)0.0073 (17)0.0073 (18)0.0118 (16)
C310.0148 (15)0.0177 (15)0.0198 (16)0.0035 (12)0.0009 (13)0.0036 (12)
C320.0226 (17)0.0196 (16)0.0171 (16)0.0007 (13)0.0001 (13)0.0002 (13)
C330.0244 (17)0.0215 (16)0.0182 (16)0.0067 (14)0.0017 (13)0.0032 (13)
C340.0179 (16)0.0275 (17)0.0209 (17)0.0038 (13)0.0050 (13)0.0052 (13)
C350.0178 (16)0.0234 (17)0.0250 (17)0.0030 (13)0.0000 (13)0.0043 (13)
C360.0291 (18)0.0312 (19)0.0194 (17)0.0021 (14)0.0048 (14)0.0041 (14)
C410.0201 (16)0.0182 (15)0.0182 (16)0.0027 (13)0.0034 (13)0.0043 (13)
C420.0225 (16)0.0197 (16)0.0192 (16)0.0032 (13)0.0027 (13)0.0018 (13)
C430.0285 (18)0.0202 (17)0.0263 (18)0.0039 (14)0.0074 (15)0.0036 (14)
C440.0306 (19)0.0204 (17)0.0318 (19)0.0062 (14)0.0087 (16)0.0011 (14)
C450.0189 (16)0.0234 (17)0.0285 (18)0.0035 (13)0.0032 (14)0.0025 (14)
C460.035 (2)0.0255 (18)0.032 (2)0.0019 (15)0.0033 (16)0.0070 (15)
C10.0195 (18)0.027 (2)0.047 (2)0.0015 (15)0.0093 (16)0.0028 (17)
N10.0272 (15)0.0195 (15)0.0351 (17)0.0007 (12)0.0108 (13)0.0007 (13)
C20.036 (2)0.035 (2)0.051 (3)0.0039 (17)0.0011 (19)0.0112 (19)
N20.0431 (19)0.046 (2)0.049 (2)0.0010 (16)0.0032 (17)0.0185 (17)
N30.055 (2)0.040 (2)0.130 (4)0.0205 (18)0.050 (3)0.045 (2)
B10.025 (2)0.039 (2)0.031 (2)0.0001 (18)0.0032 (18)0.0011 (18)
F10.0582 (15)0.0594 (16)0.0631 (17)0.0194 (12)0.0170 (13)0.0003 (13)
F20.0297 (11)0.0501 (13)0.0491 (13)0.0074 (10)0.0010 (10)0.0093 (11)
F30.0307 (11)0.0524 (14)0.0316 (11)0.0014 (9)0.0030 (9)0.0072 (10)
F40.0410 (13)0.0729 (16)0.0334 (12)0.0204 (11)0.0162 (10)0.0070 (11)
Geometric parameters (Å, º) top
Cu1—N11.980 (3)C26—H26B0.9800
Cu1—N101.985 (2)C26—H26C0.9800
Cu1—N301.986 (2)C31—C351.380 (4)
Cu1—N402.072 (2)C31—C411.478 (4)
Cu1—N202.110 (2)C32—C331.386 (4)
N10—C121.341 (4)C32—H320.9500
N10—C111.355 (4)C33—C341.392 (4)
N20—C221.342 (4)C33—C361.506 (4)
N20—C211.354 (4)C34—C351.384 (4)
N30—C321.332 (4)C34—H340.9500
N30—C311.361 (4)C35—H350.9500
N40—C421.336 (4)C36—H36A0.9800
N40—C411.347 (4)C36—H36B0.9800
C11—C151.391 (4)C36—H36C0.9800
C11—C211.473 (4)C41—C451.389 (4)
C12—C131.392 (4)C42—C431.381 (4)
C12—H120.9500C42—H420.9500
C13—C141.382 (5)C43—C441.394 (4)
C13—C161.502 (4)C43—C461.493 (4)
C14—C151.375 (5)C44—C451.385 (4)
C14—H140.9500C44—H440.9500
C15—H150.9500C45—H450.9500
C16—H16A0.9800C46—H46A0.9800
C16—H16B0.9800C46—H46B0.9800
C16—H16C0.9800C46—H46C0.9800
C21—C251.384 (4)C1—N11.136 (4)
C22—C231.393 (4)C1—N31.286 (5)
C22—H220.9500C2—N21.156 (4)
C23—C241.388 (4)C2—N31.334 (5)
C23—C261.501 (4)B1—F41.383 (4)
C24—C251.377 (5)B1—F11.387 (5)
C24—H240.9500B1—F21.394 (4)
C25—H250.9500B1—F31.398 (4)
C26—H26A0.9800
N1—Cu1—N1090.43 (10)C23—C26—H26A109.5
N1—Cu1—N3090.81 (10)C23—C26—H26B109.5
N10—Cu1—N30176.81 (10)H26A—C26—H26B109.5
N1—Cu1—N40135.33 (10)C23—C26—H26C109.5
N10—Cu1—N4096.55 (9)H26A—C26—H26C109.5
N30—Cu1—N4080.51 (9)H26B—C26—H26C109.5
N1—Cu1—N20127.09 (10)N30—C31—C35119.7 (3)
N10—Cu1—N2079.73 (9)N30—C31—C41114.9 (2)
N30—Cu1—N20101.82 (9)C35—C31—C41125.3 (3)
N40—Cu1—N2097.54 (9)N30—C32—C33123.5 (3)
C12—N10—C11119.4 (3)N30—C32—H32118.2
C12—N10—Cu1123.3 (2)C33—C32—H32118.2
C11—N10—Cu1117.0 (2)C32—C33—C34116.8 (3)
C22—N20—C21119.0 (3)C32—C33—C36120.9 (3)
C22—N20—Cu1127.7 (2)C34—C33—C36122.3 (3)
C21—N20—Cu1112.65 (19)C35—C34—C33119.9 (3)
C32—N30—C31119.8 (3)C35—C34—H34120.1
C32—N30—Cu1124.3 (2)C33—C34—H34120.1
C31—N30—Cu1115.86 (19)C31—C35—C34120.3 (3)
C42—N40—C41119.4 (3)C31—C35—H35119.9
C42—N40—Cu1126.8 (2)C34—C35—H35119.9
C41—N40—Cu1113.51 (19)C33—C36—H36A109.5
N10—C11—C15119.8 (3)C33—C36—H36B109.5
N10—C11—C21114.9 (3)H36A—C36—H36B109.5
C15—C11—C21125.3 (3)C33—C36—H36C109.5
N10—C12—C13123.6 (3)H36A—C36—H36C109.5
N10—C12—H12118.2H36B—C36—H36C109.5
C13—C12—H12118.2N40—C41—C45120.9 (3)
C14—C13—C12116.5 (3)N40—C41—C31115.1 (3)
C14—C13—C16123.2 (3)C45—C41—C31124.0 (3)
C12—C13—C16120.3 (3)N40—C42—C43123.6 (3)
C15—C14—C13120.5 (3)N40—C42—H42118.2
C15—C14—H14119.7C43—C42—H42118.2
C13—C14—H14119.7C42—C43—C44116.9 (3)
C14—C15—C11120.2 (3)C42—C43—C46121.2 (3)
C14—C15—H15119.9C44—C43—C46121.9 (3)
C11—C15—H15119.9C45—C44—C43120.3 (3)
C13—C16—H16A109.5C45—C44—H44119.9
C13—C16—H16B109.5C43—C44—H44119.9
H16A—C16—H16B109.5C44—C45—C41118.9 (3)
C13—C16—H16C109.5C44—C45—H45120.5
H16A—C16—H16C109.5C41—C45—H45120.5
H16B—C16—H16C109.5C43—C46—H46A109.5
N20—C21—C25121.2 (3)C43—C46—H46B109.5
N20—C21—C11115.3 (3)H46A—C46—H46B109.5
C25—C21—C11123.5 (3)C43—C46—H46C109.5
N20—C22—C23123.2 (3)H46A—C46—H46C109.5
N20—C22—H22118.4H46B—C46—H46C109.5
C23—C22—H22118.4N1—C1—N3173.7 (3)
C24—C23—C22116.7 (3)C1—N1—Cu1156.0 (3)
C24—C23—C26121.9 (3)N2—C2—N3174.7 (4)
C22—C23—C26121.4 (3)C1—N3—C2120.6 (3)
C25—C24—C23120.9 (3)F4—B1—F1110.1 (3)
C25—C24—H24119.6F4—B1—F2108.6 (3)
C23—C24—H24119.6F1—B1—F2110.4 (3)
C24—C25—C21119.0 (3)F4—B1—F3109.5 (3)
C24—C25—H25120.5F1—B1—F3108.5 (3)
C21—C25—H25120.5F2—B1—F3109.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···F40.952.393.217 (4)146
C36—H36B···F40.982.563.449 (4)151
C36—H36A···F4i0.982.513.367 (4)146
C14—H14···F2ii0.952.553.409 (4)150
C16—H16C···F3iii0.982.503.387 (4)150
C25—H25···N2iv0.952.533.456 (4)165
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y, z1; (iii) x+2, y+1, z+1; (iv) x+1, y+1/2, z+1/2.
(cumbdc__II) (Dicyanamido-κN1)bis(5,5'-dimethyl-2,2'-bipyridine-κ2N,N')copper(II) perchlorate top
Crystal data top
[Cu(C2N3)(C12H12N2)2]ClO4F(000) = 1228
Mr = 597.51Dx = 1.506 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16012 reflections
a = 13.6977 (11) Åθ = 2.7–26.5°
b = 16.9837 (17) ŵ = 0.98 mm1
c = 11.3416 (13) ÅT = 120 K
β = 93.146 (10)°Prism, green
V = 2634.5 (5) Å30.56 × 0.16 × 0.12 mm
Z = 4
Data collection top
Oxford MODEL? CCD area-detector
diffractometer
5160 independent reflections
Radiation source: Enhance (Mo) X-ray Source3667 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.3438 pixels mm-1θmax = 26.0°, θmin = 2.7°
Rotation method data acquisition using ω scansh = 1616
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 2020
Tmin = 0.872, Tmax = 1.000l = 1313
33629 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
5160 reflections(Δ/σ)max = 0.002
370 parametersΔρmax = 0.63 e Å3
1 restraintΔρmin = 0.27 e Å3
Special details top

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction, 2007. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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*/UeqOcc. (<1)
Cu10.754962 (18)0.500438 (15)0.47104 (2)0.01831 (10)
N100.65715 (14)0.49363 (10)0.33538 (16)0.0207 (4)
N200.64331 (12)0.57318 (10)0.53240 (15)0.0182 (4)
N300.85789 (13)0.50910 (10)0.60059 (16)0.0181 (4)
N400.83877 (13)0.58866 (10)0.40342 (16)0.0184 (4)
C110.57295 (16)0.53347 (14)0.34457 (19)0.0210 (5)
C120.66802 (18)0.44718 (13)0.2417 (2)0.0261 (5)
H120.72840.42030.23600.031*
C130.59605 (19)0.43603 (14)0.1524 (2)0.0310 (6)
C140.50977 (19)0.47793 (16)0.1621 (2)0.0334 (6)
H140.45850.47290.10280.040*
C150.49813 (17)0.52680 (16)0.2575 (2)0.0288 (6)
H150.43930.55570.26350.035*
C160.6120 (2)0.38075 (17)0.0520 (2)0.0447 (8)
H16A0.65880.40410.00030.067*
H16B0.54970.37140.00740.067*
H16C0.63790.33070.08310.067*
C210.56784 (16)0.58247 (13)0.4518 (2)0.0198 (5)
C220.64623 (16)0.61788 (13)0.6305 (2)0.0222 (5)
H220.69900.61060.68730.027*
C230.57575 (17)0.67423 (14)0.6528 (2)0.0266 (6)
C240.49826 (17)0.68116 (14)0.5704 (2)0.0284 (6)
H240.44770.71790.58340.034*
C250.49305 (16)0.63553 (14)0.4694 (2)0.0260 (6)
H250.43940.64040.41310.031*
C260.5846 (2)0.72547 (16)0.7605 (2)0.0388 (7)
H26A0.60310.77890.73770.058*
H26B0.63470.70390.81640.058*
H26C0.52170.72710.79760.058*
C310.92965 (15)0.56224 (12)0.58380 (19)0.0184 (5)
C320.86278 (16)0.46346 (14)0.69680 (19)0.0214 (5)
H320.81160.42670.70700.026*
C330.93889 (16)0.46712 (14)0.78234 (19)0.0215 (5)
C341.01200 (16)0.52194 (14)0.7661 (2)0.0239 (5)
H341.06510.52690.82310.029*
C351.00745 (16)0.56973 (13)0.6663 (2)0.0224 (5)
H351.05740.60730.65490.027*
C360.94001 (18)0.41362 (14)0.8881 (2)0.0301 (6)
H36A1.00370.41710.93140.045*
H36B0.92850.35930.86190.045*
H36C0.88850.42960.93980.045*
C410.91695 (15)0.60896 (13)0.47485 (19)0.0189 (5)
C420.81855 (16)0.63042 (13)0.3050 (2)0.0214 (5)
H420.76380.61530.25510.026*
C430.87320 (17)0.69448 (13)0.2720 (2)0.0245 (5)
C440.95485 (18)0.71361 (14)0.3445 (2)0.0273 (6)
H440.99550.75630.32400.033*
C450.97721 (17)0.67117 (14)0.4458 (2)0.0250 (5)
H451.03310.68420.49530.030*
C460.8454 (2)0.74021 (15)0.1617 (2)0.0339 (6)
H46A0.89140.72820.10100.051*
H46B0.84750.79670.17920.051*
H46C0.77910.72550.13290.051*
C10.76700 (17)0.32170 (17)0.4463 (3)0.0370 (7)
N10.76040 (14)0.38421 (12)0.47922 (17)0.0273 (5)
C20.7270 (2)0.21801 (18)0.3222 (3)0.0336 (8)0.834 (3)
N20.68284 (17)0.18252 (16)0.2545 (2)0.0337 (7)0.834 (3)
N30.7848 (3)0.25235 (19)0.4064 (4)0.0683 (13)0.834 (3)
C2B0.8092 (11)0.2081 (9)0.5873 (11)0.035 (4)*0.166 (3)
N2B0.8406 (7)0.1748 (6)0.6676 (8)0.011 (2)*0.166 (3)
N3B0.7724 (12)0.2458 (10)0.4889 (16)0.046 (4)*0.166 (3)
Cl11.24618 (4)0.42146 (4)1.03712 (5)0.03237 (17)
O11.19070 (16)0.36472 (13)1.09856 (18)0.0580 (6)
O21.32824 (13)0.38425 (11)0.98733 (17)0.0435 (5)
O31.27993 (13)0.48158 (11)1.11934 (16)0.0394 (5)
O41.18676 (13)0.45637 (13)0.94363 (16)0.0480 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02194 (16)0.01567 (16)0.01668 (16)0.00056 (12)0.00489 (11)0.00003 (11)
N100.0249 (10)0.0188 (10)0.0179 (9)0.0015 (8)0.0047 (8)0.0010 (8)
N200.0179 (9)0.0188 (10)0.0176 (10)0.0004 (8)0.0017 (8)0.0023 (8)
N300.0189 (9)0.0167 (10)0.0186 (9)0.0008 (8)0.0013 (8)0.0005 (8)
N400.0204 (9)0.0170 (10)0.0177 (10)0.0014 (8)0.0011 (8)0.0004 (8)
C110.0212 (12)0.0209 (12)0.0207 (12)0.0045 (10)0.0021 (10)0.0066 (10)
C120.0348 (14)0.0206 (13)0.0222 (12)0.0002 (11)0.0034 (11)0.0000 (10)
C130.0471 (16)0.0271 (14)0.0181 (12)0.0125 (12)0.0052 (11)0.0025 (10)
C140.0337 (15)0.0436 (17)0.0218 (13)0.0146 (12)0.0096 (11)0.0066 (11)
C150.0241 (13)0.0349 (14)0.0265 (14)0.0055 (11)0.0069 (11)0.0074 (11)
C160.069 (2)0.0397 (18)0.0238 (14)0.0111 (15)0.0082 (14)0.0043 (12)
C210.0189 (11)0.0194 (12)0.0211 (12)0.0026 (9)0.0003 (9)0.0053 (9)
C220.0235 (12)0.0211 (13)0.0220 (12)0.0002 (10)0.0003 (10)0.0006 (10)
C230.0331 (14)0.0192 (13)0.0279 (13)0.0015 (11)0.0074 (11)0.0000 (10)
C240.0239 (13)0.0245 (14)0.0372 (15)0.0065 (10)0.0054 (11)0.0060 (11)
C250.0206 (12)0.0269 (14)0.0301 (14)0.0015 (10)0.0020 (11)0.0092 (11)
C260.0459 (17)0.0351 (16)0.0356 (16)0.0080 (13)0.0049 (13)0.0099 (12)
C310.0181 (11)0.0169 (12)0.0201 (12)0.0032 (9)0.0009 (9)0.0030 (9)
C320.0262 (13)0.0179 (12)0.0197 (12)0.0003 (10)0.0027 (10)0.0004 (10)
C330.0245 (12)0.0218 (12)0.0179 (12)0.0059 (10)0.0007 (10)0.0018 (10)
C340.0215 (12)0.0281 (14)0.0212 (12)0.0044 (10)0.0055 (10)0.0040 (10)
C350.0191 (12)0.0220 (13)0.0260 (13)0.0023 (9)0.0002 (10)0.0026 (10)
C360.0319 (14)0.0345 (15)0.0233 (13)0.0033 (11)0.0054 (11)0.0053 (11)
C410.0197 (11)0.0175 (12)0.0198 (12)0.0033 (9)0.0022 (9)0.0033 (9)
C420.0233 (12)0.0206 (12)0.0202 (12)0.0039 (10)0.0002 (10)0.0009 (9)
C430.0306 (13)0.0200 (13)0.0234 (13)0.0039 (10)0.0067 (11)0.0034 (10)
C440.0316 (14)0.0193 (13)0.0317 (14)0.0043 (10)0.0088 (11)0.0025 (10)
C450.0223 (12)0.0228 (13)0.0300 (14)0.0022 (10)0.0021 (10)0.0021 (11)
C460.0427 (16)0.0286 (15)0.0309 (14)0.0018 (12)0.0050 (12)0.0094 (12)
C10.0234 (14)0.0263 (16)0.0599 (19)0.0001 (12)0.0102 (13)0.0003 (14)
N10.0295 (11)0.0192 (12)0.0317 (12)0.0016 (9)0.0114 (9)0.0009 (9)
C20.0299 (17)0.0263 (17)0.044 (2)0.0107 (14)0.0001 (16)0.0053 (15)
N20.0291 (14)0.0361 (16)0.0354 (15)0.0031 (12)0.0013 (12)0.0191 (13)
N30.065 (2)0.0374 (19)0.096 (3)0.0280 (16)0.051 (2)0.039 (2)
Cl10.0259 (3)0.0434 (4)0.0272 (3)0.0006 (3)0.0040 (3)0.0026 (3)
O10.0611 (14)0.0614 (15)0.0528 (14)0.0189 (11)0.0141 (11)0.0078 (11)
O20.0317 (10)0.0516 (13)0.0467 (12)0.0076 (9)0.0022 (9)0.0079 (10)
O30.0352 (10)0.0518 (13)0.0305 (10)0.0001 (9)0.0039 (8)0.0061 (9)
O40.0428 (11)0.0692 (15)0.0302 (10)0.0183 (10)0.0142 (9)0.0004 (10)
Geometric parameters (Å, º) top
Cu1—N11.977 (2)C26—H26C0.9800
Cu1—N301.9852 (18)C31—C351.385 (3)
Cu1—N101.9873 (18)C31—C411.471 (3)
Cu1—N402.0609 (18)C32—C331.386 (3)
Cu1—N202.1135 (18)C32—H320.9500
N10—C121.338 (3)C33—C341.387 (3)
N10—C111.346 (3)C33—C361.504 (3)
N20—C221.345 (3)C34—C351.391 (3)
N20—C211.351 (3)C34—H340.9500
N30—C321.337 (3)C35—H350.9500
N30—C311.356 (3)C36—H36A0.9800
N40—C421.339 (3)C36—H36B0.9800
N40—C411.352 (3)C36—H36C0.9800
C11—C151.389 (3)C41—C451.391 (3)
C11—C211.478 (3)C42—C431.384 (3)
C12—C131.387 (3)C42—H420.9500
C12—H120.9500C43—C441.390 (3)
C13—C141.389 (4)C43—C461.504 (3)
C13—C161.502 (4)C44—C451.377 (3)
C14—C151.379 (4)C44—H440.9500
C14—H140.9500C45—H450.9500
C15—H150.9500C46—H46A0.9800
C16—H16A0.9800C46—H46B0.9800
C16—H16B0.9800C46—H46C0.9800
C16—H16C0.9800C1—N11.131 (3)
C21—C251.387 (3)C1—N31.290 (4)
C22—C231.392 (3)C1—N3B1.378 (17)
C22—H220.9500C2—N21.126 (4)
C23—C241.380 (3)C2—N31.340 (4)
C23—C261.499 (3)C2B—N2B1.136 (5)
C24—C251.382 (3)C2B—N3B1.359 (19)
C24—H240.9500Cl1—O41.4294 (18)
C25—H250.9500Cl1—O21.4323 (19)
C26—H26A0.9800Cl1—O11.432 (2)
C26—H26B0.9800Cl1—O31.4416 (19)
N1—Cu1—N3090.91 (7)C23—C26—H26B109.5
N1—Cu1—N1090.02 (7)H26A—C26—H26B109.5
N30—Cu1—N10176.94 (7)C23—C26—H26C109.5
N1—Cu1—N40136.29 (8)H26A—C26—H26C109.5
N30—Cu1—N4080.45 (7)H26B—C26—H26C109.5
N10—Cu1—N4096.88 (7)N30—C31—C35120.2 (2)
N1—Cu1—N20126.45 (8)N30—C31—C41115.08 (19)
N30—Cu1—N20102.14 (7)C35—C31—C41124.7 (2)
N10—Cu1—N2079.61 (7)N30—C32—C33123.2 (2)
N40—Cu1—N2097.21 (7)N30—C32—H32118.4
C12—N10—C11119.4 (2)C33—C32—H32118.4
C12—N10—Cu1123.32 (16)C34—C33—C32117.3 (2)
C11—N10—Cu1117.06 (15)C34—C33—C36122.4 (2)
C22—N20—C21118.72 (19)C32—C33—C36120.4 (2)
C22—N20—Cu1127.79 (15)C33—C34—C35119.9 (2)
C21—N20—Cu1112.71 (14)C33—C34—H34120.0
C32—N30—C31119.76 (19)C35—C34—H34120.0
C32—N30—Cu1124.25 (15)C31—C35—C34119.6 (2)
C31—N30—Cu1115.87 (14)C31—C35—H35120.2
C42—N40—C41119.05 (19)C34—C35—H35120.2
C42—N40—Cu1126.97 (15)C33—C36—H36A109.5
C41—N40—Cu1113.68 (14)C33—C36—H36B109.5
N10—C11—C15120.4 (2)H36A—C36—H36B109.5
N10—C11—C21115.22 (19)C33—C36—H36C109.5
C15—C11—C21124.4 (2)H36A—C36—H36C109.5
N10—C12—C13123.7 (2)H36B—C36—H36C109.5
N10—C12—H12118.2N40—C41—C45120.8 (2)
C13—C12—H12118.2N40—C41—C31114.79 (19)
C12—C13—C14116.5 (2)C45—C41—C31124.4 (2)
C12—C13—C16120.8 (2)N40—C42—C43123.5 (2)
C14—C13—C16122.7 (2)N40—C42—H42118.3
C15—C14—C13120.4 (2)C43—C42—H42118.3
C15—C14—H14119.8C42—C43—C44117.0 (2)
C13—C14—H14119.8C42—C43—C46121.0 (2)
C14—C15—C11119.6 (2)C44—C43—C46122.0 (2)
C14—C15—H15120.2C45—C44—C43120.4 (2)
C11—C15—H15120.2C45—C44—H44119.8
C13—C16—H16A109.5C43—C44—H44119.8
C13—C16—H16B109.5C44—C45—C41119.2 (2)
H16A—C16—H16B109.5C44—C45—H45120.4
C13—C16—H16C109.5C41—C45—H45120.4
H16A—C16—H16C109.5C43—C46—H46A109.5
H16B—C16—H16C109.5C43—C46—H46B109.5
N20—C21—C25121.5 (2)H46A—C46—H46B109.5
N20—C21—C11114.95 (19)C43—C46—H46C109.5
C25—C21—C11123.6 (2)H46A—C46—H46C109.5
N20—C22—C23123.3 (2)H46B—C46—H46C109.5
N20—C22—H22118.4N1—C1—N3173.4 (3)
C23—C22—H22118.4N1—C1—N3B140.1 (8)
C24—C23—C22116.8 (2)C1—N1—Cu1157.7 (2)
C24—C23—C26121.8 (2)N2—C2—N3173.3 (3)
C22—C23—C26121.4 (2)C1—N3—C2122.1 (3)
C23—C24—C25121.1 (2)N2B—C2B—N3B178.0 (18)
C23—C24—H24119.5O4—Cl1—O2108.52 (11)
C25—C24—H24119.5O4—Cl1—O1110.14 (13)
C24—C25—C21118.6 (2)O2—Cl1—O1110.11 (13)
C24—C25—H25120.7O4—Cl1—O3109.60 (13)
C21—C25—H25120.7O2—Cl1—O3109.67 (11)
C23—C26—H26A109.5O1—Cl1—O3108.78 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···O40.952.413.240 (3)145
C36—H36A···O40.982.593.481 (3)151
C36—H36C···O4i0.982.593.449 (3)146
C16—H16A···O3ii0.982.533.428 (3)151
C25—H25···N2iii0.952.573.495 (3)166
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+2, y+1, z+1; (iii) x+1, y+1/2, z+1/2.
Selected geometric parameters (Å, °) in (I) and (II) top
(I)(II)
Cu1—N11.980 (3)1.977 (2)
Cu1—N101.985 (2)1.9873 (18)
Cu1—N202.110 (2)2.1135 (18)
Cu1—N301.986 (2)1.9852 (18)
Cu1—N402.072 (2)2.0609 (18)
N1—Cu1—N1090.43 (10)90.02 (7)
N1—Cu1—N20127.09 (10)126.45 (8)
N1—Cu1—N3090.81 (10)90.91 (7)
N1—Cu1—N40135.33 (10)136.29 (8)
N10—Cu1—N2079.73 (9)79.61 (7)
N10—Cu1—N30176.81 (10)176.94 (7)
N10—Cu1—N4096.55 (9)96.88 (7)
N30—Cu1—N20101.82 (9)102.14 (7)
N30—Cu1—N4080.51 (9)80.45 (7)
N40—Cu1—N2097.54 (9)97.21 (7)
 

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