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(Dicyanamido-κ
N1)bis(5,5′-dimethyl-2,2′-bipyridine-κ
2N,
N′)copper(II) tetrafluoroborate, [Cu{N(CN)
2}(C
12H
12N
2)
2]BF
4, (I), and (dicyanamido-κ
N1)bis(5,5′-dimethyl-2,2′-bipyridine-κ
2N,
N′)copper(II) perchlorate, [Cu{N(CN)
2}(C
12H
12N
2)
2]ClO
4, (II), are isomorphous and consist of [Cu{N(CN)
2}(mbpy)
2]
+ cations (mbpy is 5,5′-dimethyl-2,2′-bipyridine) and BF
4− or ClO
4− anions, respectively. The Cu
II 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—N
mbpy bonds have very similar values [1.986 (1) Å on average] and are shorter than the other two equatorial Cu—N
mbpy 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
CCDC references: 964425; 964426
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]BF4 | F(000) = 1196 |
Mr = 584.87 | Dx = 1.488 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10476 reflections |
a = 13.6714 (8) Å | θ = 2.6–26.5° |
b = 17.0453 (17) Å | µ = 0.90 mm−1 |
c = 11.2195 (11) Å | T = 120 K |
β = 93.361 (7)° | Prism, dark green-blue |
V = 2610.0 (4) Å3 | 0.62 × 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 Source | 3476 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 8.3438 pixels mm-1 | θmax = 26.0°, θmin = 2.7° |
Rotation method data acquisition using ω scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −21→21 |
Tmin = 0.902, Tmax = 1.000 | l = −13→13 |
31369 measured reflections | |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-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 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.75447 (2) | 0.50007 (2) | 0.47088 (3) | 0.01707 (13) | |
N10 | 0.65590 (17) | 0.49331 (13) | 0.3342 (2) | 0.0175 (5) | |
N20 | 0.64331 (17) | 0.57242 (14) | 0.5336 (2) | 0.0174 (5) | |
N30 | 0.85829 (17) | 0.50938 (13) | 0.6016 (2) | 0.0166 (5) | |
N40 | 0.83855 (17) | 0.58789 (14) | 0.4005 (2) | 0.0177 (5) | |
C11 | 0.5709 (2) | 0.53307 (18) | 0.3440 (3) | 0.0191 (7) | |
C12 | 0.6662 (2) | 0.44677 (17) | 0.2394 (3) | 0.0238 (7) | |
H12 | 0.7265 | 0.4198 | 0.2336 | 0.029* | |
C13 | 0.5933 (2) | 0.43577 (18) | 0.1490 (3) | 0.0255 (7) | |
C14 | 0.5070 (2) | 0.4768 (2) | 0.1597 (3) | 0.0280 (8) | |
H14 | 0.4551 | 0.4714 | 0.1002 | 0.034* | |
C15 | 0.4957 (2) | 0.52530 (19) | 0.2559 (3) | 0.0250 (7) | |
H15 | 0.4363 | 0.5536 | 0.2621 | 0.030* | |
C16 | 0.6100 (3) | 0.3815 (2) | 0.0468 (3) | 0.0381 (9) | |
H16A | 0.5483 | 0.3740 | −0.0010 | 0.057* | |
H16B | 0.6334 | 0.3307 | 0.0780 | 0.057* | |
H16C | 0.6590 | 0.4042 | −0.0032 | 0.057* | |
C21 | 0.5669 (2) | 0.58142 (17) | 0.4524 (3) | 0.0183 (7) | |
C22 | 0.6471 (2) | 0.61666 (17) | 0.6327 (3) | 0.0210 (7) | |
H22 | 0.7005 | 0.6094 | 0.6897 | 0.025* | |
C23 | 0.5765 (2) | 0.67266 (18) | 0.6561 (3) | 0.0239 (7) | |
C24 | 0.4978 (2) | 0.67950 (19) | 0.5728 (3) | 0.0262 (7) | |
H24 | 0.4470 | 0.7160 | 0.5861 | 0.031* | |
C25 | 0.4923 (2) | 0.63415 (18) | 0.4711 (3) | 0.0239 (7) | |
H25 | 0.4382 | 0.6390 | 0.4145 | 0.029* | |
C26 | 0.5858 (3) | 0.7232 (2) | 0.7657 (3) | 0.0372 (9) | |
H26A | 0.6128 | 0.7744 | 0.7452 | 0.056* | |
H26B | 0.6296 | 0.6978 | 0.8263 | 0.056* | |
H26C | 0.5211 | 0.7305 | 0.7973 | 0.056* | |
C31 | 0.9303 (2) | 0.56246 (16) | 0.5837 (3) | 0.0174 (6) | |
C32 | 0.8636 (2) | 0.46468 (18) | 0.6991 (3) | 0.0198 (7) | |
H32 | 0.8122 | 0.4283 | 0.7100 | 0.024* | |
C33 | 0.9400 (2) | 0.46838 (19) | 0.7857 (3) | 0.0213 (7) | |
C34 | 1.0138 (2) | 0.52262 (18) | 0.7676 (3) | 0.0224 (7) | |
H34 | 1.0679 | 0.5274 | 0.8243 | 0.027* | |
C35 | 1.0083 (2) | 0.56964 (18) | 0.6669 (3) | 0.0221 (7) | |
H35 | 1.0583 | 0.6070 | 0.6549 | 0.027* | |
C36 | 0.9422 (2) | 0.41545 (18) | 0.8932 (3) | 0.0268 (8) | |
H36A | 0.8901 | 0.4308 | 0.9449 | 0.040* | |
H36B | 1.0059 | 0.4201 | 0.9375 | 0.040* | |
H36C | 0.9321 | 0.3610 | 0.8673 | 0.040* | |
C41 | 0.9166 (2) | 0.60861 (17) | 0.4725 (3) | 0.0188 (7) | |
C42 | 0.8174 (2) | 0.62878 (17) | 0.3008 (3) | 0.0204 (7) | |
H42 | 0.7621 | 0.6133 | 0.2510 | 0.024* | |
C43 | 0.8715 (2) | 0.69235 (18) | 0.2660 (3) | 0.0247 (7) | |
C44 | 0.9534 (2) | 0.71257 (18) | 0.3394 (3) | 0.0273 (8) | |
H44 | 0.9934 | 0.7554 | 0.3185 | 0.033* | |
C45 | 0.9767 (2) | 0.67043 (18) | 0.4427 (3) | 0.0235 (7) | |
H45 | 1.0330 | 0.6836 | 0.4924 | 0.028* | |
C46 | 0.8429 (3) | 0.73715 (19) | 0.1550 (3) | 0.0309 (8) | |
H46A | 0.8887 | 0.7252 | 0.0936 | 0.046* | |
H46B | 0.8446 | 0.7935 | 0.1723 | 0.046* | |
H46C | 0.7764 | 0.7221 | 0.1262 | 0.046* | |
C1 | 0.7693 (2) | 0.3224 (2) | 0.4426 (3) | 0.0319 (8) | |
N1 | 0.76171 (18) | 0.38416 (16) | 0.4790 (2) | 0.0278 (6) | |
C2 | 0.7297 (3) | 0.2187 (2) | 0.3215 (4) | 0.0410 (10) | |
N2 | 0.6823 (2) | 0.18364 (19) | 0.2513 (3) | 0.0463 (9) | |
N3 | 0.7878 (3) | 0.2528 (2) | 0.4060 (4) | 0.0772 (15) | |
B1 | 1.2455 (3) | 0.4243 (3) | 1.0386 (4) | 0.0318 (9) | |
F1 | 1.19149 (18) | 0.37021 (14) | 1.0997 (2) | 0.0597 (7) | |
F2 | 1.32476 (14) | 0.38772 (12) | 0.98906 (19) | 0.0431 (5) | |
F3 | 1.27936 (14) | 0.48226 (12) | 1.11884 (18) | 0.0384 (5) | |
F4 | 1.18741 (15) | 0.45822 (14) | 0.94757 (19) | 0.0498 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0175 (2) | 0.0165 (2) | 0.0167 (2) | 0.00030 (15) | −0.00310 (14) | −0.00015 (15) |
N10 | 0.0167 (13) | 0.0182 (13) | 0.0176 (13) | −0.0008 (11) | 0.0000 (10) | 0.0002 (11) |
N20 | 0.0171 (13) | 0.0176 (13) | 0.0174 (13) | −0.0006 (10) | 0.0006 (11) | 0.0035 (10) |
N30 | 0.0148 (12) | 0.0165 (13) | 0.0184 (13) | 0.0009 (10) | 0.0003 (10) | −0.0020 (10) |
N40 | 0.0174 (13) | 0.0186 (13) | 0.0172 (13) | 0.0013 (10) | 0.0022 (11) | −0.0006 (10) |
C11 | 0.0193 (16) | 0.0183 (15) | 0.0198 (16) | −0.0033 (13) | 0.0018 (13) | 0.0063 (13) |
C12 | 0.0248 (17) | 0.0221 (17) | 0.0244 (17) | −0.0013 (13) | −0.0002 (14) | 0.0028 (14) |
C13 | 0.0325 (19) | 0.0272 (18) | 0.0163 (16) | −0.0077 (15) | −0.0022 (14) | 0.0027 (13) |
C14 | 0.0226 (18) | 0.041 (2) | 0.0193 (17) | −0.0102 (15) | −0.0073 (14) | 0.0031 (15) |
C15 | 0.0200 (17) | 0.0319 (18) | 0.0225 (17) | −0.0036 (14) | −0.0036 (14) | 0.0062 (14) |
C16 | 0.055 (2) | 0.038 (2) | 0.0209 (18) | −0.0046 (18) | −0.0053 (17) | −0.0048 (16) |
C21 | 0.0167 (15) | 0.0213 (16) | 0.0173 (16) | −0.0024 (12) | 0.0027 (13) | 0.0032 (12) |
C22 | 0.0204 (16) | 0.0235 (17) | 0.0192 (16) | −0.0028 (13) | 0.0009 (13) | −0.0009 (13) |
C23 | 0.0277 (18) | 0.0189 (16) | 0.0258 (18) | −0.0013 (14) | 0.0076 (14) | 0.0001 (13) |
C24 | 0.0237 (17) | 0.0216 (17) | 0.034 (2) | 0.0045 (14) | 0.0066 (15) | 0.0037 (15) |
C25 | 0.0170 (16) | 0.0225 (17) | 0.032 (2) | 0.0008 (13) | −0.0021 (14) | 0.0090 (14) |
C26 | 0.044 (2) | 0.033 (2) | 0.035 (2) | 0.0073 (17) | 0.0073 (18) | −0.0118 (16) |
C31 | 0.0148 (15) | 0.0177 (15) | 0.0198 (16) | 0.0035 (12) | 0.0009 (13) | −0.0036 (12) |
C32 | 0.0226 (17) | 0.0196 (16) | 0.0171 (16) | −0.0007 (13) | 0.0001 (13) | 0.0002 (13) |
C33 | 0.0244 (17) | 0.0215 (16) | 0.0182 (16) | 0.0067 (14) | 0.0017 (13) | −0.0032 (13) |
C34 | 0.0179 (16) | 0.0275 (17) | 0.0209 (17) | 0.0038 (13) | −0.0050 (13) | −0.0052 (13) |
C35 | 0.0178 (16) | 0.0234 (17) | 0.0250 (17) | −0.0030 (13) | 0.0000 (13) | −0.0043 (13) |
C36 | 0.0291 (18) | 0.0312 (19) | 0.0194 (17) | 0.0021 (14) | −0.0048 (14) | 0.0041 (14) |
C41 | 0.0201 (16) | 0.0182 (15) | 0.0182 (16) | 0.0027 (13) | 0.0034 (13) | −0.0043 (13) |
C42 | 0.0225 (16) | 0.0197 (16) | 0.0192 (16) | 0.0032 (13) | 0.0027 (13) | 0.0018 (13) |
C43 | 0.0285 (18) | 0.0202 (17) | 0.0263 (18) | 0.0039 (14) | 0.0074 (15) | 0.0036 (14) |
C44 | 0.0306 (19) | 0.0204 (17) | 0.0318 (19) | −0.0062 (14) | 0.0087 (16) | 0.0011 (14) |
C45 | 0.0189 (16) | 0.0234 (17) | 0.0285 (18) | −0.0035 (13) | 0.0032 (14) | −0.0025 (14) |
C46 | 0.035 (2) | 0.0255 (18) | 0.032 (2) | −0.0019 (15) | 0.0033 (16) | 0.0070 (15) |
C1 | 0.0195 (18) | 0.027 (2) | 0.047 (2) | −0.0015 (15) | −0.0093 (16) | −0.0028 (17) |
N1 | 0.0272 (15) | 0.0195 (15) | 0.0351 (17) | −0.0007 (12) | −0.0108 (13) | 0.0007 (13) |
C2 | 0.036 (2) | 0.035 (2) | 0.051 (3) | 0.0039 (17) | −0.0011 (19) | −0.0112 (19) |
N2 | 0.0431 (19) | 0.046 (2) | 0.049 (2) | −0.0010 (16) | −0.0032 (17) | −0.0185 (17) |
N3 | 0.055 (2) | 0.040 (2) | 0.130 (4) | 0.0205 (18) | −0.050 (3) | −0.045 (2) |
B1 | 0.025 (2) | 0.039 (2) | 0.031 (2) | −0.0001 (18) | −0.0032 (18) | −0.0011 (18) |
F1 | 0.0582 (15) | 0.0594 (16) | 0.0631 (17) | −0.0194 (12) | 0.0170 (13) | −0.0003 (13) |
F2 | 0.0297 (11) | 0.0501 (13) | 0.0491 (13) | 0.0074 (10) | −0.0010 (10) | −0.0093 (11) |
F3 | 0.0307 (11) | 0.0524 (14) | 0.0316 (11) | −0.0014 (9) | −0.0030 (9) | −0.0072 (10) |
F4 | 0.0410 (13) | 0.0729 (16) | 0.0334 (12) | 0.0204 (11) | −0.0162 (10) | −0.0070 (11) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.980 (3) | C26—H26B | 0.9800 |
Cu1—N10 | 1.985 (2) | C26—H26C | 0.9800 |
Cu1—N30 | 1.986 (2) | C31—C35 | 1.380 (4) |
Cu1—N40 | 2.072 (2) | C31—C41 | 1.478 (4) |
Cu1—N20 | 2.110 (2) | C32—C33 | 1.386 (4) |
N10—C12 | 1.341 (4) | C32—H32 | 0.9500 |
N10—C11 | 1.355 (4) | C33—C34 | 1.392 (4) |
N20—C22 | 1.342 (4) | C33—C36 | 1.506 (4) |
N20—C21 | 1.354 (4) | C34—C35 | 1.384 (4) |
N30—C32 | 1.332 (4) | C34—H34 | 0.9500 |
N30—C31 | 1.361 (4) | C35—H35 | 0.9500 |
N40—C42 | 1.336 (4) | C36—H36A | 0.9800 |
N40—C41 | 1.347 (4) | C36—H36B | 0.9800 |
C11—C15 | 1.391 (4) | C36—H36C | 0.9800 |
C11—C21 | 1.473 (4) | C41—C45 | 1.389 (4) |
C12—C13 | 1.392 (4) | C42—C43 | 1.381 (4) |
C12—H12 | 0.9500 | C42—H42 | 0.9500 |
C13—C14 | 1.382 (5) | C43—C44 | 1.394 (4) |
C13—C16 | 1.502 (4) | C43—C46 | 1.493 (4) |
C14—C15 | 1.375 (5) | C44—C45 | 1.385 (4) |
C14—H14 | 0.9500 | C44—H44 | 0.9500 |
C15—H15 | 0.9500 | C45—H45 | 0.9500 |
C16—H16A | 0.9800 | C46—H46A | 0.9800 |
C16—H16B | 0.9800 | C46—H46B | 0.9800 |
C16—H16C | 0.9800 | C46—H46C | 0.9800 |
C21—C25 | 1.384 (4) | C1—N1 | 1.136 (4) |
C22—C23 | 1.393 (4) | C1—N3 | 1.286 (5) |
C22—H22 | 0.9500 | C2—N2 | 1.156 (4) |
C23—C24 | 1.388 (4) | C2—N3 | 1.334 (5) |
C23—C26 | 1.501 (4) | B1—F4 | 1.383 (4) |
C24—C25 | 1.377 (5) | B1—F1 | 1.387 (5) |
C24—H24 | 0.9500 | B1—F2 | 1.394 (4) |
C25—H25 | 0.9500 | B1—F3 | 1.398 (4) |
C26—H26A | 0.9800 | | |
| | | |
N1—Cu1—N10 | 90.43 (10) | C23—C26—H26A | 109.5 |
N1—Cu1—N30 | 90.81 (10) | C23—C26—H26B | 109.5 |
N10—Cu1—N30 | 176.81 (10) | H26A—C26—H26B | 109.5 |
N1—Cu1—N40 | 135.33 (10) | C23—C26—H26C | 109.5 |
N10—Cu1—N40 | 96.55 (9) | H26A—C26—H26C | 109.5 |
N30—Cu1—N40 | 80.51 (9) | H26B—C26—H26C | 109.5 |
N1—Cu1—N20 | 127.09 (10) | N30—C31—C35 | 119.7 (3) |
N10—Cu1—N20 | 79.73 (9) | N30—C31—C41 | 114.9 (2) |
N30—Cu1—N20 | 101.82 (9) | C35—C31—C41 | 125.3 (3) |
N40—Cu1—N20 | 97.54 (9) | N30—C32—C33 | 123.5 (3) |
C12—N10—C11 | 119.4 (3) | N30—C32—H32 | 118.2 |
C12—N10—Cu1 | 123.3 (2) | C33—C32—H32 | 118.2 |
C11—N10—Cu1 | 117.0 (2) | C32—C33—C34 | 116.8 (3) |
C22—N20—C21 | 119.0 (3) | C32—C33—C36 | 120.9 (3) |
C22—N20—Cu1 | 127.7 (2) | C34—C33—C36 | 122.3 (3) |
C21—N20—Cu1 | 112.65 (19) | C35—C34—C33 | 119.9 (3) |
C32—N30—C31 | 119.8 (3) | C35—C34—H34 | 120.1 |
C32—N30—Cu1 | 124.3 (2) | C33—C34—H34 | 120.1 |
C31—N30—Cu1 | 115.86 (19) | C31—C35—C34 | 120.3 (3) |
C42—N40—C41 | 119.4 (3) | C31—C35—H35 | 119.9 |
C42—N40—Cu1 | 126.8 (2) | C34—C35—H35 | 119.9 |
C41—N40—Cu1 | 113.51 (19) | C33—C36—H36A | 109.5 |
N10—C11—C15 | 119.8 (3) | C33—C36—H36B | 109.5 |
N10—C11—C21 | 114.9 (3) | H36A—C36—H36B | 109.5 |
C15—C11—C21 | 125.3 (3) | C33—C36—H36C | 109.5 |
N10—C12—C13 | 123.6 (3) | H36A—C36—H36C | 109.5 |
N10—C12—H12 | 118.2 | H36B—C36—H36C | 109.5 |
C13—C12—H12 | 118.2 | N40—C41—C45 | 120.9 (3) |
C14—C13—C12 | 116.5 (3) | N40—C41—C31 | 115.1 (3) |
C14—C13—C16 | 123.2 (3) | C45—C41—C31 | 124.0 (3) |
C12—C13—C16 | 120.3 (3) | N40—C42—C43 | 123.6 (3) |
C15—C14—C13 | 120.5 (3) | N40—C42—H42 | 118.2 |
C15—C14—H14 | 119.7 | C43—C42—H42 | 118.2 |
C13—C14—H14 | 119.7 | C42—C43—C44 | 116.9 (3) |
C14—C15—C11 | 120.2 (3) | C42—C43—C46 | 121.2 (3) |
C14—C15—H15 | 119.9 | C44—C43—C46 | 121.9 (3) |
C11—C15—H15 | 119.9 | C45—C44—C43 | 120.3 (3) |
C13—C16—H16A | 109.5 | C45—C44—H44 | 119.9 |
C13—C16—H16B | 109.5 | C43—C44—H44 | 119.9 |
H16A—C16—H16B | 109.5 | C44—C45—C41 | 118.9 (3) |
C13—C16—H16C | 109.5 | C44—C45—H45 | 120.5 |
H16A—C16—H16C | 109.5 | C41—C45—H45 | 120.5 |
H16B—C16—H16C | 109.5 | C43—C46—H46A | 109.5 |
N20—C21—C25 | 121.2 (3) | C43—C46—H46B | 109.5 |
N20—C21—C11 | 115.3 (3) | H46A—C46—H46B | 109.5 |
C25—C21—C11 | 123.5 (3) | C43—C46—H46C | 109.5 |
N20—C22—C23 | 123.2 (3) | H46A—C46—H46C | 109.5 |
N20—C22—H22 | 118.4 | H46B—C46—H46C | 109.5 |
C23—C22—H22 | 118.4 | N1—C1—N3 | 173.7 (3) |
C24—C23—C22 | 116.7 (3) | C1—N1—Cu1 | 156.0 (3) |
C24—C23—C26 | 121.9 (3) | N2—C2—N3 | 174.7 (4) |
C22—C23—C26 | 121.4 (3) | C1—N3—C2 | 120.6 (3) |
C25—C24—C23 | 120.9 (3) | F4—B1—F1 | 110.1 (3) |
C25—C24—H24 | 119.6 | F4—B1—F2 | 108.6 (3) |
C23—C24—H24 | 119.6 | F1—B1—F2 | 110.4 (3) |
C24—C25—C21 | 119.0 (3) | F4—B1—F3 | 109.5 (3) |
C24—C25—H25 | 120.5 | F1—B1—F3 | 108.5 (3) |
C21—C25—H25 | 120.5 | F2—B1—F3 | 109.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···F4 | 0.95 | 2.39 | 3.217 (4) | 146 |
C36—H36B···F4 | 0.98 | 2.56 | 3.449 (4) | 151 |
C36—H36A···F4i | 0.98 | 2.51 | 3.367 (4) | 146 |
C14—H14···F2ii | 0.95 | 2.55 | 3.409 (4) | 150 |
C16—H16C···F3iii | 0.98 | 2.50 | 3.387 (4) | 150 |
C25—H25···N2iv | 0.95 | 2.53 | 3.456 (4) | 165 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z−1; (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]ClO4 | F(000) = 1228 |
Mr = 597.51 | Dx = 1.506 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 16012 reflections |
a = 13.6977 (11) Å | θ = 2.7–26.5° |
b = 16.9837 (17) Å | µ = 0.98 mm−1 |
c = 11.3416 (13) Å | T = 120 K |
β = 93.146 (10)° | Prism, green |
V = 2634.5 (5) Å3 | 0.56 × 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 Source | 3667 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.3438 pixels mm-1 | θmax = 26.0°, θmin = 2.7° |
Rotation method data acquisition using ω scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −20→20 |
Tmin = 0.872, Tmax = 1.000 | l = −13→13 |
33629 measured reflections | |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-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 parameters | Δρmax = 0.63 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.754962 (18) | 0.500438 (15) | 0.47104 (2) | 0.01831 (10) | |
N10 | 0.65715 (14) | 0.49363 (10) | 0.33538 (16) | 0.0207 (4) | |
N20 | 0.64331 (12) | 0.57318 (10) | 0.53240 (15) | 0.0182 (4) | |
N30 | 0.85789 (13) | 0.50910 (10) | 0.60059 (16) | 0.0181 (4) | |
N40 | 0.83877 (13) | 0.58866 (10) | 0.40342 (16) | 0.0184 (4) | |
C11 | 0.57295 (16) | 0.53347 (14) | 0.34457 (19) | 0.0210 (5) | |
C12 | 0.66802 (18) | 0.44718 (13) | 0.2417 (2) | 0.0261 (5) | |
H12 | 0.7284 | 0.4203 | 0.2360 | 0.031* | |
C13 | 0.59605 (19) | 0.43603 (14) | 0.1524 (2) | 0.0310 (6) | |
C14 | 0.50977 (19) | 0.47793 (16) | 0.1621 (2) | 0.0334 (6) | |
H14 | 0.4585 | 0.4729 | 0.1028 | 0.040* | |
C15 | 0.49813 (17) | 0.52680 (16) | 0.2575 (2) | 0.0288 (6) | |
H15 | 0.4393 | 0.5557 | 0.2635 | 0.035* | |
C16 | 0.6120 (2) | 0.38075 (17) | 0.0520 (2) | 0.0447 (8) | |
H16A | 0.6588 | 0.4041 | −0.0003 | 0.067* | |
H16B | 0.5497 | 0.3714 | 0.0074 | 0.067* | |
H16C | 0.6379 | 0.3307 | 0.0831 | 0.067* | |
C21 | 0.56784 (16) | 0.58247 (13) | 0.4518 (2) | 0.0198 (5) | |
C22 | 0.64623 (16) | 0.61788 (13) | 0.6305 (2) | 0.0222 (5) | |
H22 | 0.6990 | 0.6106 | 0.6873 | 0.027* | |
C23 | 0.57575 (17) | 0.67423 (14) | 0.6528 (2) | 0.0266 (6) | |
C24 | 0.49826 (17) | 0.68116 (14) | 0.5704 (2) | 0.0284 (6) | |
H24 | 0.4477 | 0.7179 | 0.5834 | 0.034* | |
C25 | 0.49305 (16) | 0.63553 (14) | 0.4694 (2) | 0.0260 (6) | |
H25 | 0.4394 | 0.6404 | 0.4131 | 0.031* | |
C26 | 0.5846 (2) | 0.72547 (16) | 0.7605 (2) | 0.0388 (7) | |
H26A | 0.6031 | 0.7789 | 0.7377 | 0.058* | |
H26B | 0.6347 | 0.7039 | 0.8164 | 0.058* | |
H26C | 0.5217 | 0.7271 | 0.7976 | 0.058* | |
C31 | 0.92965 (15) | 0.56224 (12) | 0.58380 (19) | 0.0184 (5) | |
C32 | 0.86278 (16) | 0.46346 (14) | 0.69680 (19) | 0.0214 (5) | |
H32 | 0.8116 | 0.4267 | 0.7070 | 0.026* | |
C33 | 0.93889 (16) | 0.46712 (14) | 0.78234 (19) | 0.0215 (5) | |
C34 | 1.01200 (16) | 0.52194 (14) | 0.7661 (2) | 0.0239 (5) | |
H34 | 1.0651 | 0.5269 | 0.8231 | 0.029* | |
C35 | 1.00745 (16) | 0.56973 (13) | 0.6663 (2) | 0.0224 (5) | |
H35 | 1.0574 | 0.6073 | 0.6549 | 0.027* | |
C36 | 0.94001 (18) | 0.41362 (14) | 0.8881 (2) | 0.0301 (6) | |
H36A | 1.0037 | 0.4171 | 0.9314 | 0.045* | |
H36B | 0.9285 | 0.3593 | 0.8619 | 0.045* | |
H36C | 0.8885 | 0.4296 | 0.9398 | 0.045* | |
C41 | 0.91695 (15) | 0.60896 (13) | 0.47485 (19) | 0.0189 (5) | |
C42 | 0.81855 (16) | 0.63042 (13) | 0.3050 (2) | 0.0214 (5) | |
H42 | 0.7638 | 0.6153 | 0.2551 | 0.026* | |
C43 | 0.87320 (17) | 0.69448 (13) | 0.2720 (2) | 0.0245 (5) | |
C44 | 0.95485 (18) | 0.71361 (14) | 0.3445 (2) | 0.0273 (6) | |
H44 | 0.9955 | 0.7563 | 0.3240 | 0.033* | |
C45 | 0.97721 (17) | 0.67117 (14) | 0.4458 (2) | 0.0250 (5) | |
H45 | 1.0331 | 0.6842 | 0.4953 | 0.030* | |
C46 | 0.8454 (2) | 0.74021 (15) | 0.1617 (2) | 0.0339 (6) | |
H46A | 0.8914 | 0.7282 | 0.1010 | 0.051* | |
H46B | 0.8475 | 0.7967 | 0.1792 | 0.051* | |
H46C | 0.7791 | 0.7255 | 0.1329 | 0.051* | |
C1 | 0.76700 (17) | 0.32170 (17) | 0.4463 (3) | 0.0370 (7) | |
N1 | 0.76040 (14) | 0.38421 (12) | 0.47922 (17) | 0.0273 (5) | |
C2 | 0.7270 (2) | 0.21801 (18) | 0.3222 (3) | 0.0336 (8) | 0.834 (3) |
N2 | 0.68284 (17) | 0.18252 (16) | 0.2545 (2) | 0.0337 (7) | 0.834 (3) |
N3 | 0.7848 (3) | 0.25235 (19) | 0.4064 (4) | 0.0683 (13) | 0.834 (3) |
C2B | 0.8092 (11) | 0.2081 (9) | 0.5873 (11) | 0.035 (4)* | 0.166 (3) |
N2B | 0.8406 (7) | 0.1748 (6) | 0.6676 (8) | 0.011 (2)* | 0.166 (3) |
N3B | 0.7724 (12) | 0.2458 (10) | 0.4889 (16) | 0.046 (4)* | 0.166 (3) |
Cl1 | 1.24618 (4) | 0.42146 (4) | 1.03712 (5) | 0.03237 (17) | |
O1 | 1.19070 (16) | 0.36472 (13) | 1.09856 (18) | 0.0580 (6) | |
O2 | 1.32824 (13) | 0.38425 (11) | 0.98733 (17) | 0.0435 (5) | |
O3 | 1.27993 (13) | 0.48158 (11) | 1.11934 (16) | 0.0394 (5) | |
O4 | 1.18676 (13) | 0.45637 (13) | 0.94363 (16) | 0.0480 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02194 (16) | 0.01567 (16) | 0.01668 (16) | 0.00056 (12) | −0.00489 (11) | −0.00003 (11) |
N10 | 0.0249 (10) | 0.0188 (10) | 0.0179 (9) | −0.0015 (8) | −0.0047 (8) | 0.0010 (8) |
N20 | 0.0179 (9) | 0.0188 (10) | 0.0176 (10) | −0.0004 (8) | −0.0017 (8) | 0.0023 (8) |
N30 | 0.0189 (9) | 0.0167 (10) | 0.0186 (9) | 0.0008 (8) | −0.0013 (8) | −0.0005 (8) |
N40 | 0.0204 (9) | 0.0170 (10) | 0.0177 (10) | 0.0014 (8) | 0.0011 (8) | 0.0004 (8) |
C11 | 0.0212 (12) | 0.0209 (12) | 0.0207 (12) | −0.0045 (10) | −0.0021 (10) | 0.0066 (10) |
C12 | 0.0348 (14) | 0.0206 (13) | 0.0222 (12) | −0.0002 (11) | −0.0034 (11) | 0.0000 (10) |
C13 | 0.0471 (16) | 0.0271 (14) | 0.0181 (12) | −0.0125 (12) | −0.0052 (11) | 0.0025 (10) |
C14 | 0.0337 (15) | 0.0436 (17) | 0.0218 (13) | −0.0146 (12) | −0.0096 (11) | 0.0066 (11) |
C15 | 0.0241 (13) | 0.0349 (14) | 0.0265 (14) | −0.0055 (11) | −0.0069 (11) | 0.0074 (11) |
C16 | 0.069 (2) | 0.0397 (18) | 0.0238 (14) | −0.0111 (15) | −0.0082 (14) | −0.0043 (12) |
C21 | 0.0189 (11) | 0.0194 (12) | 0.0211 (12) | −0.0026 (9) | −0.0003 (9) | 0.0053 (9) |
C22 | 0.0235 (12) | 0.0211 (13) | 0.0220 (12) | −0.0002 (10) | 0.0003 (10) | 0.0006 (10) |
C23 | 0.0331 (14) | 0.0192 (13) | 0.0279 (13) | 0.0015 (11) | 0.0074 (11) | 0.0000 (10) |
C24 | 0.0239 (13) | 0.0245 (14) | 0.0372 (15) | 0.0065 (10) | 0.0054 (11) | 0.0060 (11) |
C25 | 0.0206 (12) | 0.0269 (14) | 0.0301 (14) | 0.0015 (10) | −0.0020 (11) | 0.0092 (11) |
C26 | 0.0459 (17) | 0.0351 (16) | 0.0356 (16) | 0.0080 (13) | 0.0049 (13) | −0.0099 (12) |
C31 | 0.0181 (11) | 0.0169 (12) | 0.0201 (12) | 0.0032 (9) | 0.0009 (9) | −0.0030 (9) |
C32 | 0.0262 (13) | 0.0179 (12) | 0.0197 (12) | 0.0003 (10) | −0.0027 (10) | −0.0004 (10) |
C33 | 0.0245 (12) | 0.0218 (12) | 0.0179 (12) | 0.0059 (10) | −0.0007 (10) | −0.0018 (10) |
C34 | 0.0215 (12) | 0.0281 (14) | 0.0212 (12) | 0.0044 (10) | −0.0055 (10) | −0.0040 (10) |
C35 | 0.0191 (12) | 0.0220 (13) | 0.0260 (13) | −0.0023 (9) | −0.0002 (10) | −0.0026 (10) |
C36 | 0.0319 (14) | 0.0345 (15) | 0.0233 (13) | 0.0033 (11) | −0.0054 (11) | 0.0053 (11) |
C41 | 0.0197 (11) | 0.0175 (12) | 0.0198 (12) | 0.0033 (9) | 0.0022 (9) | −0.0033 (9) |
C42 | 0.0233 (12) | 0.0206 (12) | 0.0202 (12) | 0.0039 (10) | 0.0002 (10) | 0.0009 (9) |
C43 | 0.0306 (13) | 0.0200 (13) | 0.0234 (13) | 0.0039 (10) | 0.0067 (11) | 0.0034 (10) |
C44 | 0.0316 (14) | 0.0193 (13) | 0.0317 (14) | −0.0043 (10) | 0.0088 (11) | 0.0025 (10) |
C45 | 0.0223 (12) | 0.0228 (13) | 0.0300 (14) | −0.0022 (10) | 0.0021 (10) | −0.0021 (11) |
C46 | 0.0427 (16) | 0.0286 (15) | 0.0309 (14) | 0.0018 (12) | 0.0050 (12) | 0.0094 (12) |
C1 | 0.0234 (14) | 0.0263 (16) | 0.0599 (19) | 0.0001 (12) | −0.0102 (13) | 0.0003 (14) |
N1 | 0.0295 (11) | 0.0192 (12) | 0.0317 (12) | −0.0016 (9) | −0.0114 (9) | 0.0009 (9) |
C2 | 0.0299 (17) | 0.0263 (17) | 0.044 (2) | 0.0107 (14) | 0.0001 (16) | −0.0053 (15) |
N2 | 0.0291 (14) | 0.0361 (16) | 0.0354 (15) | −0.0031 (12) | −0.0013 (12) | −0.0191 (13) |
N3 | 0.065 (2) | 0.0374 (19) | 0.096 (3) | 0.0280 (16) | −0.051 (2) | −0.039 (2) |
Cl1 | 0.0259 (3) | 0.0434 (4) | 0.0272 (3) | 0.0006 (3) | −0.0040 (3) | 0.0026 (3) |
O1 | 0.0611 (14) | 0.0614 (15) | 0.0528 (14) | −0.0189 (11) | 0.0141 (11) | 0.0078 (11) |
O2 | 0.0317 (10) | 0.0516 (13) | 0.0467 (12) | 0.0076 (9) | −0.0022 (9) | −0.0079 (10) |
O3 | 0.0352 (10) | 0.0518 (13) | 0.0305 (10) | 0.0001 (9) | −0.0039 (8) | −0.0061 (9) |
O4 | 0.0428 (11) | 0.0692 (15) | 0.0302 (10) | 0.0183 (10) | −0.0142 (9) | 0.0004 (10) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.977 (2) | C26—H26C | 0.9800 |
Cu1—N30 | 1.9852 (18) | C31—C35 | 1.385 (3) |
Cu1—N10 | 1.9873 (18) | C31—C41 | 1.471 (3) |
Cu1—N40 | 2.0609 (18) | C32—C33 | 1.386 (3) |
Cu1—N20 | 2.1135 (18) | C32—H32 | 0.9500 |
N10—C12 | 1.338 (3) | C33—C34 | 1.387 (3) |
N10—C11 | 1.346 (3) | C33—C36 | 1.504 (3) |
N20—C22 | 1.345 (3) | C34—C35 | 1.391 (3) |
N20—C21 | 1.351 (3) | C34—H34 | 0.9500 |
N30—C32 | 1.337 (3) | C35—H35 | 0.9500 |
N30—C31 | 1.356 (3) | C36—H36A | 0.9800 |
N40—C42 | 1.339 (3) | C36—H36B | 0.9800 |
N40—C41 | 1.352 (3) | C36—H36C | 0.9800 |
C11—C15 | 1.389 (3) | C41—C45 | 1.391 (3) |
C11—C21 | 1.478 (3) | C42—C43 | 1.384 (3) |
C12—C13 | 1.387 (3) | C42—H42 | 0.9500 |
C12—H12 | 0.9500 | C43—C44 | 1.390 (3) |
C13—C14 | 1.389 (4) | C43—C46 | 1.504 (3) |
C13—C16 | 1.502 (4) | C44—C45 | 1.377 (3) |
C14—C15 | 1.379 (4) | C44—H44 | 0.9500 |
C14—H14 | 0.9500 | C45—H45 | 0.9500 |
C15—H15 | 0.9500 | C46—H46A | 0.9800 |
C16—H16A | 0.9800 | C46—H46B | 0.9800 |
C16—H16B | 0.9800 | C46—H46C | 0.9800 |
C16—H16C | 0.9800 | C1—N1 | 1.131 (3) |
C21—C25 | 1.387 (3) | C1—N3 | 1.290 (4) |
C22—C23 | 1.392 (3) | C1—N3B | 1.378 (17) |
C22—H22 | 0.9500 | C2—N2 | 1.126 (4) |
C23—C24 | 1.380 (3) | C2—N3 | 1.340 (4) |
C23—C26 | 1.499 (3) | C2B—N2B | 1.136 (5) |
C24—C25 | 1.382 (3) | C2B—N3B | 1.359 (19) |
C24—H24 | 0.9500 | Cl1—O4 | 1.4294 (18) |
C25—H25 | 0.9500 | Cl1—O2 | 1.4323 (19) |
C26—H26A | 0.9800 | Cl1—O1 | 1.432 (2) |
C26—H26B | 0.9800 | Cl1—O3 | 1.4416 (19) |
| | | |
N1—Cu1—N30 | 90.91 (7) | C23—C26—H26B | 109.5 |
N1—Cu1—N10 | 90.02 (7) | H26A—C26—H26B | 109.5 |
N30—Cu1—N10 | 176.94 (7) | C23—C26—H26C | 109.5 |
N1—Cu1—N40 | 136.29 (8) | H26A—C26—H26C | 109.5 |
N30—Cu1—N40 | 80.45 (7) | H26B—C26—H26C | 109.5 |
N10—Cu1—N40 | 96.88 (7) | N30—C31—C35 | 120.2 (2) |
N1—Cu1—N20 | 126.45 (8) | N30—C31—C41 | 115.08 (19) |
N30—Cu1—N20 | 102.14 (7) | C35—C31—C41 | 124.7 (2) |
N10—Cu1—N20 | 79.61 (7) | N30—C32—C33 | 123.2 (2) |
N40—Cu1—N20 | 97.21 (7) | N30—C32—H32 | 118.4 |
C12—N10—C11 | 119.4 (2) | C33—C32—H32 | 118.4 |
C12—N10—Cu1 | 123.32 (16) | C34—C33—C32 | 117.3 (2) |
C11—N10—Cu1 | 117.06 (15) | C34—C33—C36 | 122.4 (2) |
C22—N20—C21 | 118.72 (19) | C32—C33—C36 | 120.4 (2) |
C22—N20—Cu1 | 127.79 (15) | C33—C34—C35 | 119.9 (2) |
C21—N20—Cu1 | 112.71 (14) | C33—C34—H34 | 120.0 |
C32—N30—C31 | 119.76 (19) | C35—C34—H34 | 120.0 |
C32—N30—Cu1 | 124.25 (15) | C31—C35—C34 | 119.6 (2) |
C31—N30—Cu1 | 115.87 (14) | C31—C35—H35 | 120.2 |
C42—N40—C41 | 119.05 (19) | C34—C35—H35 | 120.2 |
C42—N40—Cu1 | 126.97 (15) | C33—C36—H36A | 109.5 |
C41—N40—Cu1 | 113.68 (14) | C33—C36—H36B | 109.5 |
N10—C11—C15 | 120.4 (2) | H36A—C36—H36B | 109.5 |
N10—C11—C21 | 115.22 (19) | C33—C36—H36C | 109.5 |
C15—C11—C21 | 124.4 (2) | H36A—C36—H36C | 109.5 |
N10—C12—C13 | 123.7 (2) | H36B—C36—H36C | 109.5 |
N10—C12—H12 | 118.2 | N40—C41—C45 | 120.8 (2) |
C13—C12—H12 | 118.2 | N40—C41—C31 | 114.79 (19) |
C12—C13—C14 | 116.5 (2) | C45—C41—C31 | 124.4 (2) |
C12—C13—C16 | 120.8 (2) | N40—C42—C43 | 123.5 (2) |
C14—C13—C16 | 122.7 (2) | N40—C42—H42 | 118.3 |
C15—C14—C13 | 120.4 (2) | C43—C42—H42 | 118.3 |
C15—C14—H14 | 119.8 | C42—C43—C44 | 117.0 (2) |
C13—C14—H14 | 119.8 | C42—C43—C46 | 121.0 (2) |
C14—C15—C11 | 119.6 (2) | C44—C43—C46 | 122.0 (2) |
C14—C15—H15 | 120.2 | C45—C44—C43 | 120.4 (2) |
C11—C15—H15 | 120.2 | C45—C44—H44 | 119.8 |
C13—C16—H16A | 109.5 | C43—C44—H44 | 119.8 |
C13—C16—H16B | 109.5 | C44—C45—C41 | 119.2 (2) |
H16A—C16—H16B | 109.5 | C44—C45—H45 | 120.4 |
C13—C16—H16C | 109.5 | C41—C45—H45 | 120.4 |
H16A—C16—H16C | 109.5 | C43—C46—H46A | 109.5 |
H16B—C16—H16C | 109.5 | C43—C46—H46B | 109.5 |
N20—C21—C25 | 121.5 (2) | H46A—C46—H46B | 109.5 |
N20—C21—C11 | 114.95 (19) | C43—C46—H46C | 109.5 |
C25—C21—C11 | 123.6 (2) | H46A—C46—H46C | 109.5 |
N20—C22—C23 | 123.3 (2) | H46B—C46—H46C | 109.5 |
N20—C22—H22 | 118.4 | N1—C1—N3 | 173.4 (3) |
C23—C22—H22 | 118.4 | N1—C1—N3B | 140.1 (8) |
C24—C23—C22 | 116.8 (2) | C1—N1—Cu1 | 157.7 (2) |
C24—C23—C26 | 121.8 (2) | N2—C2—N3 | 173.3 (3) |
C22—C23—C26 | 121.4 (2) | C1—N3—C2 | 122.1 (3) |
C23—C24—C25 | 121.1 (2) | N2B—C2B—N3B | 178.0 (18) |
C23—C24—H24 | 119.5 | O4—Cl1—O2 | 108.52 (11) |
C25—C24—H24 | 119.5 | O4—Cl1—O1 | 110.14 (13) |
C24—C25—C21 | 118.6 (2) | O2—Cl1—O1 | 110.11 (13) |
C24—C25—H25 | 120.7 | O4—Cl1—O3 | 109.60 (13) |
C21—C25—H25 | 120.7 | O2—Cl1—O3 | 109.67 (11) |
C23—C26—H26A | 109.5 | O1—Cl1—O3 | 108.78 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···O4 | 0.95 | 2.41 | 3.240 (3) | 145 |
C36—H36A···O4 | 0.98 | 2.59 | 3.481 (3) | 151 |
C36—H36C···O4i | 0.98 | 2.59 | 3.449 (3) | 146 |
C16—H16A···O3ii | 0.98 | 2.53 | 3.428 (3) | 151 |
C25—H25···N2iii | 0.95 | 2.57 | 3.495 (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—N1 | 1.980 (3) | 1.977 (2) |
Cu1—N10 | 1.985 (2) | 1.9873 (18) |
Cu1—N20 | 2.110 (2) | 2.1135 (18) |
Cu1—N30 | 1.986 (2) | 1.9852 (18) |
Cu1—N40 | 2.072 (2) | 2.0609 (18) |
N1—Cu1—N10 | 90.43 (10) | 90.02 (7) |
N1—Cu1—N20 | 127.09 (10) | 126.45 (8) |
N1—Cu1—N30 | 90.81 (10) | 90.91 (7) |
N1—Cu1—N40 | 135.33 (10) | 136.29 (8) |
N10—Cu1—N20 | 79.73 (9) | 79.61 (7) |
N10—Cu1—N30 | 176.81 (10) | 176.94 (7) |
N10—Cu1—N40 | 96.55 (9) | 96.88 (7) |
N30—Cu1—N20 | 101.82 (9) | 102.14 (7) |
N30—Cu1—N40 | 80.51 (9) | 80.45 (7) |
N40—Cu1—N20 | 97.54 (9) | 97.21 (7) |
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