In the title complex, [Cu(C
14H
37N
6)](ClO
4)
3, the Cu
II atom adopts a slightly distorted trigonal bipyramidal coordination and one amino group in the complex is protonated. The Cu—N bond distances in the equatorial plane are in the range 2.074 (4)–2.173 (4) Å. Two N atoms occupy the axial positions with Cu—N contacts of 2.048 (3) and 2.056 (3) Å. All of the perchlorate anions are disordered. In the crystal structure, there are many N—H
O intermolecular hydrogen bonds between cations and anions, forming a three-dimensional network.
Supporting information
CCDC reference: 618109
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.060
- wR factor = 0.146
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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.
[
N,
N,
N'-Tris(3-aminopropyl)-
N'-(3-ammoniopropyl)ethane-1,2-diamine]copper(II) tris(perchlorate)
top
Crystal data top
[Cu(C14H37N6)](ClO4)3 | F(000) = 1356 |
Mr = 651.39 | Dx = 1.634 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1517 reflections |
a = 9.3315 (11) Å | θ = 2.0–25.3° |
b = 18.131 (2) Å | µ = 1.19 mm−1 |
c = 15.8484 (18) Å | T = 298 K |
β = 99.092 (2)° | Needle, blue |
V = 2647.7 (5) Å3 | 0.30 × 0.10 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5180 independent reflections |
Radiation source: sealed tube | 4129 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.716, Tmax = 0.911 | k = −21→22 |
14355 measured reflections | l = −15→19 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.08P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3 |
5180 reflections | (Δ/σ)max < 0.001 |
464 parameters | Δρmax = 0.48 e Å−3 |
174 restraints | Δρmin = −0.65 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 | Occ. (<1) |
C1 | 0.5039 (5) | 0.3500 (3) | 0.7152 (3) | 0.0445 (11) | |
H1A | 0.4859 | 0.3546 | 0.6534 | 0.053* | |
H1B | 0.4298 | 0.3783 | 0.7374 | 0.053* | |
C2 | 0.4884 (5) | 0.2700 (2) | 0.7383 (3) | 0.0385 (10) | |
H2A | 0.5154 | 0.2646 | 0.7996 | 0.046* | |
H2B | 0.3872 | 0.2559 | 0.7235 | 0.046* | |
C3 | 0.5792 (5) | 0.2182 (3) | 0.6945 (3) | 0.0491 (12) | |
H3A | 0.5555 | 0.1677 | 0.7071 | 0.059* | |
H3B | 0.5567 | 0.2252 | 0.6332 | 0.059* | |
C4 | 0.8061 (6) | 0.3215 (2) | 0.5035 (3) | 0.0415 (10) | |
H4A | 0.7020 | 0.3160 | 0.5003 | 0.050* | |
H4B | 0.8352 | 0.2954 | 0.4555 | 0.050* | |
C5 | 0.8431 (5) | 0.4023 (3) | 0.4980 (3) | 0.0426 (11) | |
H5A | 0.7994 | 0.4206 | 0.4424 | 0.051* | |
H5B | 0.9475 | 0.4069 | 0.5018 | 0.051* | |
C6 | 0.7947 (5) | 0.4509 (3) | 0.5657 (3) | 0.0467 (11) | |
H6A | 0.8144 | 0.5017 | 0.5523 | 0.056* | |
H6B | 0.6903 | 0.4459 | 0.5617 | 0.056* | |
C7 | 1.0198 (5) | 0.4548 (3) | 0.6685 (3) | 0.0437 (11) | |
H7A | 1.0614 | 0.4309 | 0.6233 | 0.052* | |
H7B | 1.0287 | 0.5076 | 0.6608 | 0.052* | |
C8 | 1.1108 (6) | 0.4348 (3) | 0.7514 (3) | 0.0468 (12) | |
H8A | 1.0675 | 0.4567 | 0.7972 | 0.056* | |
H8B | 1.2058 | 0.4569 | 0.7529 | 0.056* | |
C9 | 1.1313 (5) | 0.3534 (3) | 0.7697 (3) | 0.0406 (10) | |
H9A | 1.1599 | 0.3293 | 0.7202 | 0.049* | |
H9B | 1.2092 | 0.3468 | 0.8174 | 0.049* | |
C10 | 0.7911 (5) | 0.4867 (2) | 0.7135 (3) | 0.0345 (9) | |
H10A | 0.8506 | 0.4882 | 0.7695 | 0.041* | |
H10B | 0.7858 | 0.5364 | 0.6904 | 0.041* | |
C11 | 0.6471 (6) | 0.4620 (3) | 0.7219 (3) | 0.0467 (11) | |
H11A | 0.5833 | 0.4685 | 0.6679 | 0.056* | |
H11B | 0.6099 | 0.4918 | 0.7645 | 0.056* | |
C12 | 0.6849 (5) | 0.3778 (2) | 0.8414 (3) | 0.0328 (9) | |
H12A | 0.7774 | 0.4023 | 0.8581 | 0.039* | |
H12B | 0.6992 | 0.3261 | 0.8561 | 0.039* | |
C13 | 0.5780 (5) | 0.4094 (3) | 0.8958 (3) | 0.0357 (9) | |
H13A | 0.5916 | 0.4624 | 0.9004 | 0.043* | |
H13B | 0.4798 | 0.4004 | 0.8672 | 0.043* | |
C14 | 0.5954 (5) | 0.3770 (3) | 0.9838 (3) | 0.0457 (11) | |
H14A | 0.5283 | 0.4011 | 1.0158 | 0.055* | |
H14B | 0.5701 | 0.3251 | 0.9794 | 0.055* | |
Cl1 | 0.71595 (18) | 0.67798 (9) | 0.52118 (10) | 0.0392 (15) | 0.852 (6) |
Cl2 | 0.8357 (3) | 0.58682 (11) | 0.97950 (15) | 0.0387 (13) | 0.780 (13) |
Cl3 | 0.3691 (2) | 0.62631 (9) | 0.76560 (13) | 0.0347 (6) | 0.741 (5) |
Cl1' | 0.7230 (11) | 0.6815 (6) | 0.5201 (5) | 0.047 (10) | 0.148 (6) |
Cl2' | 0.8301 (12) | 0.5897 (4) | 0.9852 (7) | 0.045 (5) | 0.220 (13) |
Cl3' | 0.3453 (7) | 0.6246 (3) | 0.7469 (4) | 0.049 (3) | 0.259 (5) |
Cu1 | 0.81160 (5) | 0.33207 (3) | 0.69232 (3) | 0.03006 (16) | |
N1 | 0.6472 (4) | 0.3829 (2) | 0.7475 (2) | 0.0379 (8) | |
N2 | 1.0020 (4) | 0.3186 (2) | 0.7895 (2) | 0.0373 (8) | |
H2C | 0.9823 | 0.3372 | 0.8390 | 0.045* | |
H2D | 1.0194 | 0.2701 | 0.7975 | 0.045* | |
N3 | 0.8802 (4) | 0.2892 (2) | 0.5841 (2) | 0.0421 (9) | |
H3C | 0.9763 | 0.2969 | 0.5878 | 0.051* | |
H3D | 0.8652 | 0.2402 | 0.5827 | 0.051* | |
N4 | 0.7363 (4) | 0.2310 (2) | 0.7229 (2) | 0.0390 (8) | |
H4C | 0.7862 | 0.1959 | 0.6998 | 0.047* | |
H4D | 0.7553 | 0.2255 | 0.7801 | 0.047* | |
N5 | 0.8614 (4) | 0.43657 (19) | 0.6557 (2) | 0.0368 (8) | |
N6 | 0.7449 (4) | 0.3845 (2) | 1.0316 (2) | 0.0381 (8) | |
H6C | 0.8000 | 0.3482 | 1.0167 | 0.057* | |
H6D | 0.7425 | 0.3821 | 1.0874 | 0.057* | |
H6E | 0.7817 | 0.4277 | 1.0192 | 0.057* | |
O1 | 0.6336 (3) | 0.74011 (16) | 0.53495 (19) | 0.0415 (10) | 0.852 (6) |
O2 | 0.8171 (3) | 0.66373 (15) | 0.59450 (16) | 0.0432 (11) | 0.852 (6) |
O3 | 0.6241 (3) | 0.61700 (16) | 0.50323 (19) | 0.0444 (12) | 0.852 (6) |
O4 | 0.7891 (3) | 0.69108 (16) | 0.45199 (17) | 0.0388 (10) | 0.852 (6) |
O5 | 0.9536 (4) | 0.6257 (3) | 1.0211 (3) | 0.0434 (15) | 0.780 (13) |
O6 | 0.7765 (6) | 0.5447 (2) | 1.0381 (3) | 0.042 (2) | 0.780 (13) |
O7 | 0.7324 (4) | 0.6357 (3) | 0.9401 (3) | 0.0390 (15) | 0.780 (13) |
O8 | 0.8801 (5) | 0.5412 (2) | 0.9187 (3) | 0.0417 (15) | 0.780 (13) |
O9 | 0.3879 (4) | 0.55943 (15) | 0.8103 (2) | 0.0439 (11) | 0.741 (5) |
O10 | 0.3693 (4) | 0.68463 (16) | 0.82366 (19) | 0.0473 (12) | 0.741 (5) |
O11 | 0.2365 (4) | 0.62522 (18) | 0.7100 (2) | 0.0469 (13) | 0.741 (5) |
O12 | 0.4827 (4) | 0.63597 (18) | 0.7184 (2) | 0.0517 (13) | 0.741 (5) |
O1' | 0.6470 (18) | 0.7434 (9) | 0.4841 (10) | 0.045 (6) | 0.148 (6) |
O2' | 0.8715 (12) | 0.6910 (10) | 0.5189 (11) | 0.044 (6) | 0.148 (6) |
O3' | 0.6993 (18) | 0.6728 (9) | 0.6046 (7) | 0.036 (5) | 0.148 (6) |
O4' | 0.674 (2) | 0.6186 (9) | 0.4727 (11) | 0.061 (9) | 0.148 (6) |
O5' | 0.9751 (13) | 0.5895 (11) | 1.0214 (10) | 0.052 (6) | 0.220 (13) |
O6' | 0.754 (2) | 0.5411 (8) | 1.0291 (12) | 0.045 (8) | 0.220 (13) |
O7' | 0.7742 (17) | 0.6600 (6) | 0.9899 (14) | 0.054 (6) | 0.220 (13) |
O8' | 0.817 (2) | 0.5683 (9) | 0.9006 (7) | 0.055 (5) | 0.220 (13) |
O9' | 0.3671 (12) | 0.5585 (4) | 0.7048 (6) | 0.064 (5) | 0.259 (5) |
O10' | 0.3219 (12) | 0.6821 (5) | 0.6873 (6) | 0.054 (4) | 0.259 (5) |
O11' | 0.2240 (9) | 0.6174 (6) | 0.7884 (6) | 0.045 (3) | 0.259 (5) |
O12' | 0.4682 (9) | 0.6402 (6) | 0.8073 (6) | 0.058 (4) | 0.259 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.034 (2) | 0.054 (3) | 0.041 (2) | 0.013 (2) | −0.0039 (19) | −0.012 (2) |
C2 | 0.033 (2) | 0.036 (2) | 0.046 (2) | −0.0123 (18) | 0.0074 (19) | −0.0121 (19) |
C3 | 0.047 (3) | 0.056 (3) | 0.044 (3) | −0.015 (2) | 0.006 (2) | −0.021 (2) |
C4 | 0.051 (3) | 0.040 (2) | 0.036 (2) | −0.002 (2) | 0.014 (2) | −0.0104 (19) |
C5 | 0.046 (3) | 0.040 (2) | 0.044 (3) | 0.012 (2) | 0.014 (2) | 0.0106 (19) |
C6 | 0.043 (3) | 0.044 (3) | 0.054 (3) | 0.014 (2) | 0.012 (2) | 0.013 (2) |
C7 | 0.042 (3) | 0.041 (2) | 0.052 (3) | −0.015 (2) | 0.019 (2) | 0.002 (2) |
C8 | 0.054 (3) | 0.044 (3) | 0.042 (3) | −0.016 (2) | 0.007 (2) | −0.015 (2) |
C9 | 0.039 (2) | 0.050 (3) | 0.034 (2) | −0.004 (2) | 0.0117 (18) | −0.0113 (19) |
C10 | 0.047 (3) | 0.027 (2) | 0.033 (2) | 0.0010 (17) | 0.0156 (18) | 0.0032 (16) |
C11 | 0.052 (3) | 0.041 (3) | 0.047 (3) | 0.011 (2) | 0.009 (2) | 0.007 (2) |
C12 | 0.034 (2) | 0.0246 (19) | 0.041 (2) | 0.0035 (16) | 0.0089 (18) | −0.0041 (17) |
C13 | 0.034 (2) | 0.044 (2) | 0.031 (2) | 0.0126 (18) | 0.0133 (17) | −0.0055 (18) |
C14 | 0.039 (3) | 0.046 (3) | 0.058 (3) | 0.008 (2) | 0.026 (2) | 0.004 (2) |
Cl1 | 0.037 (2) | 0.0355 (19) | 0.044 (3) | 0.0044 (14) | 0.0022 (17) | 0.0047 (16) |
Cl2 | 0.035 (2) | 0.033 (2) | 0.048 (2) | −0.0057 (16) | 0.0033 (16) | 0.0030 (16) |
Cl3 | 0.0384 (12) | 0.0327 (12) | 0.0358 (10) | −0.0003 (9) | 0.0146 (9) | −0.0003 (8) |
Cl1' | 0.042 (14) | 0.063 (16) | 0.034 (15) | −0.007 (11) | −0.003 (10) | −0.022 (10) |
Cl2' | 0.052 (10) | 0.033 (8) | 0.054 (9) | 0.008 (7) | 0.020 (7) | 0.011 (6) |
Cl3' | 0.052 (5) | 0.046 (4) | 0.053 (4) | −0.011 (3) | 0.018 (4) | −0.016 (3) |
Cu1 | 0.0271 (3) | 0.0352 (3) | 0.0290 (3) | 0.0007 (2) | 0.00765 (18) | −0.0010 (2) |
N1 | 0.041 (2) | 0.0354 (19) | 0.0378 (19) | 0.0132 (16) | 0.0070 (15) | 0.0080 (15) |
N2 | 0.0311 (19) | 0.0383 (19) | 0.042 (2) | 0.0042 (15) | 0.0052 (15) | −0.0001 (16) |
N3 | 0.045 (2) | 0.039 (2) | 0.045 (2) | 0.0018 (17) | 0.0125 (17) | −0.0087 (16) |
N4 | 0.042 (2) | 0.0365 (19) | 0.043 (2) | −0.0036 (15) | 0.0201 (17) | 0.0035 (16) |
N5 | 0.041 (2) | 0.0309 (18) | 0.043 (2) | 0.0034 (15) | 0.0204 (16) | 0.0032 (15) |
N6 | 0.042 (2) | 0.044 (2) | 0.0324 (18) | 0.0046 (16) | 0.0167 (15) | 0.0060 (16) |
O1 | 0.041 (2) | 0.043 (2) | 0.042 (2) | 0.0188 (17) | 0.0096 (19) | −0.0057 (19) |
O2 | 0.044 (3) | 0.042 (2) | 0.037 (2) | −0.0023 (16) | −0.0151 (17) | −0.0031 (15) |
O3 | 0.043 (3) | 0.038 (2) | 0.045 (2) | −0.0158 (19) | −0.015 (2) | 0.0161 (18) |
O4 | 0.039 (2) | 0.039 (2) | 0.040 (2) | −0.0023 (15) | 0.0129 (17) | 0.0091 (16) |
O5 | 0.051 (3) | 0.043 (3) | 0.039 (2) | −0.015 (2) | 0.014 (2) | −0.011 (2) |
O6 | 0.046 (4) | 0.041 (5) | 0.040 (4) | −0.017 (3) | 0.008 (3) | 0.011 (3) |
O7 | 0.038 (2) | 0.038 (3) | 0.043 (3) | 0.0132 (19) | 0.013 (2) | 0.012 (2) |
O8 | 0.041 (3) | 0.047 (3) | 0.040 (3) | −0.016 (2) | 0.013 (2) | −0.015 (2) |
O9 | 0.044 (3) | 0.042 (2) | 0.048 (2) | −0.0044 (19) | 0.0146 (19) | −0.0120 (19) |
O10 | 0.053 (3) | 0.051 (3) | 0.040 (2) | −0.009 (2) | 0.014 (2) | 0.006 (2) |
O11 | 0.040 (3) | 0.052 (3) | 0.042 (3) | 0.011 (2) | −0.012 (2) | −0.016 (2) |
O12 | 0.050 (3) | 0.052 (3) | 0.056 (3) | −0.015 (2) | 0.015 (2) | −0.004 (2) |
O1' | 0.041 (13) | 0.036 (12) | 0.052 (16) | 0.004 (10) | −0.012 (12) | 0.019 (12) |
O2' | 0.033 (12) | 0.049 (13) | 0.053 (14) | 0.002 (9) | 0.014 (10) | −0.002 (10) |
O3' | 0.044 (13) | 0.035 (11) | 0.033 (11) | 0.006 (9) | 0.016 (9) | 0.018 (8) |
O4' | 0.055 (19) | 0.067 (18) | 0.061 (19) | −0.035 (14) | 0.006 (14) | −0.028 (15) |
O5' | 0.060 (12) | 0.047 (14) | 0.052 (10) | −0.014 (9) | 0.018 (8) | −0.012 (10) |
O6' | 0.059 (15) | 0.029 (14) | 0.045 (14) | −0.012 (11) | 0.006 (11) | 0.016 (11) |
O7' | 0.046 (10) | 0.045 (10) | 0.066 (15) | 0.004 (7) | −0.002 (9) | 0.002 (9) |
O8' | 0.066 (14) | 0.052 (11) | 0.051 (11) | 0.025 (9) | 0.016 (9) | 0.019 (8) |
O9' | 0.062 (9) | 0.055 (9) | 0.063 (9) | 0.023 (7) | −0.021 (7) | −0.021 (7) |
O10' | 0.064 (10) | 0.057 (9) | 0.042 (7) | −0.009 (7) | 0.009 (6) | 0.011 (6) |
O11' | 0.054 (8) | 0.052 (7) | 0.030 (6) | −0.009 (6) | 0.007 (5) | 0.023 (5) |
O12' | 0.067 (11) | 0.050 (8) | 0.066 (10) | −0.003 (7) | 0.037 (9) | −0.009 (7) |
Geometric parameters (Å, º) top
C1—N1 | 1.480 (6) | C13—H13B | 0.9700 |
C1—C2 | 1.509 (7) | C14—N6 | 1.484 (6) |
C1—H1A | 0.9700 | C14—H14A | 0.9700 |
C1—H1B | 0.9700 | C14—H14B | 0.9700 |
C2—C3 | 1.506 (7) | Cl1—O1 | 1.4002 (18) |
C2—H2A | 0.9700 | Cl1—O4 | 1.4003 (18) |
C2—H2B | 0.9700 | Cl1—O2 | 1.4003 (18) |
C3—N4 | 1.483 (6) | Cl1—O3 | 1.4003 (18) |
C3—H3A | 0.9700 | Cl2—O5 | 1.383 (2) |
C3—H3B | 0.9700 | Cl2—O8 | 1.383 (2) |
C4—N3 | 1.474 (6) | Cl2—O7 | 1.383 (2) |
C4—C5 | 1.510 (6) | Cl2—O6 | 1.383 (2) |
C4—H4A | 0.9700 | Cl3—O9 | 1.401 (2) |
C4—H4B | 0.9700 | Cl3—O10 | 1.401 (2) |
C5—C6 | 1.511 (7) | Cl3—O11 | 1.401 (2) |
C5—H5A | 0.9700 | Cl3—O12 | 1.402 (2) |
C5—H5B | 0.9700 | Cl1'—O2' | 1.4002 (19) |
C6—N5 | 1.486 (6) | Cl1'—O3' | 1.4003 (19) |
C6—H6A | 0.9700 | Cl1'—O4' | 1.4004 (19) |
C6—H6B | 0.9700 | Cl1'—O1' | 1.4004 (19) |
C7—C8 | 1.492 (7) | Cl2'—O5' | 1.383 (2) |
C7—N5 | 1.497 (6) | Cl2'—O6' | 1.383 (2) |
C7—H7A | 0.9700 | Cl2'—O7' | 1.383 (2) |
C7—H7B | 0.9700 | Cl2'—O8' | 1.383 (2) |
C8—C9 | 1.511 (7) | Cl3'—O11' | 1.401 (2) |
C8—H8A | 0.9700 | Cl3'—O9' | 1.401 (2) |
C8—H8B | 0.9700 | Cl3'—O12' | 1.401 (2) |
C9—N2 | 1.440 (6) | Cl3'—O10' | 1.401 (2) |
C9—H9A | 0.9700 | Cu1—N4 | 2.048 (3) |
C9—H9B | 0.9700 | Cu1—N5 | 2.056 (3) |
C10—C11 | 1.443 (7) | Cu1—N3 | 2.074 (4) |
C10—N5 | 1.512 (5) | Cu1—N1 | 2.096 (4) |
C10—H10A | 0.9700 | Cu1—N2 | 2.173 (4) |
C10—H10B | 0.9700 | N2—H2C | 0.9000 |
C11—N1 | 1.489 (6) | N2—H2D | 0.9000 |
C11—H11A | 0.9700 | N3—H3C | 0.9000 |
C11—H11B | 0.9700 | N3—H3D | 0.9000 |
C12—N1 | 1.477 (5) | N4—H4C | 0.9000 |
C12—C13 | 1.530 (5) | N4—H4D | 0.9000 |
C12—H12A | 0.9700 | N6—H6C | 0.8900 |
C12—H12B | 0.9700 | N6—H6D | 0.8900 |
C13—C14 | 1.499 (6) | N6—H6E | 0.8900 |
C13—H13A | 0.9700 | | |
| | | |
N1—C1—C2 | 114.8 (4) | H14A—C14—H14B | 107.8 |
N1—C1—H1A | 108.6 | O1—Cl1—O4 | 109.46 (6) |
C2—C1—H1A | 108.6 | O1—Cl1—O2 | 109.48 (6) |
N1—C1—H1B | 108.6 | O4—Cl1—O2 | 109.48 (6) |
C2—C1—H1B | 108.6 | O1—Cl1—O3 | 109.47 (6) |
H1A—C1—H1B | 107.5 | O4—Cl1—O3 | 109.46 (6) |
C3—C2—C1 | 113.9 (4) | O2—Cl1—O3 | 109.48 (6) |
C3—C2—H2A | 108.8 | O5—Cl2—O8 | 109.49 (6) |
C1—C2—H2A | 108.8 | O5—Cl2—O7 | 109.49 (6) |
C3—C2—H2B | 108.8 | O8—Cl2—O7 | 109.47 (6) |
C1—C2—H2B | 108.8 | O5—Cl2—O6 | 109.47 (6) |
H2A—C2—H2B | 107.7 | O8—Cl2—O6 | 109.45 (6) |
N4—C3—C2 | 111.4 (4) | O7—Cl2—O6 | 109.47 (6) |
N4—C3—H3A | 109.4 | O9—Cl3—O10 | 109.50 (6) |
C2—C3—H3A | 109.4 | O9—Cl3—O11 | 109.47 (6) |
N4—C3—H3B | 109.4 | O10—Cl3—O11 | 109.46 (6) |
C2—C3—H3B | 109.4 | O9—Cl3—O12 | 109.46 (6) |
H3A—C3—H3B | 108.0 | O10—Cl3—O12 | 109.47 (6) |
N3—C4—C5 | 110.8 (4) | O11—Cl3—O12 | 109.47 (6) |
N3—C4—H4A | 109.5 | O2'—Cl1'—O3' | 109.48 (6) |
C5—C4—H4A | 109.5 | O2'—Cl1'—O4' | 109.47 (6) |
N3—C4—H4B | 109.5 | O3'—Cl1'—O4' | 109.48 (6) |
C5—C4—H4B | 109.5 | O2'—Cl1'—O1' | 109.48 (6) |
H4A—C4—H4B | 108.1 | O3'—Cl1'—O1' | 109.47 (6) |
C4—C5—C6 | 115.3 (4) | O4'—Cl1'—O1' | 109.46 (6) |
C4—C5—H5A | 108.4 | O5'—Cl2'—O6' | 109.47 (6) |
C6—C5—H5A | 108.4 | O5'—Cl2'—O7' | 109.47 (7) |
C4—C5—H5B | 108.4 | O6'—Cl2'—O7' | 109.47 (6) |
C6—C5—H5B | 108.4 | O5'—Cl2'—O8' | 109.47 (6) |
H5A—C5—H5B | 107.5 | O6'—Cl2'—O8' | 109.47 (7) |
N5—C6—C5 | 116.9 (4) | O7'—Cl2'—O8' | 109.47 (6) |
N5—C6—H6A | 108.1 | O11'—Cl3'—O9' | 109.47 (6) |
C5—C6—H6A | 108.1 | O11'—Cl3'—O12' | 109.48 (6) |
N5—C6—H6B | 108.1 | O9'—Cl3'—O12' | 109.47 (6) |
C5—C6—H6B | 108.1 | O11'—Cl3'—O10' | 109.47 (6) |
H6A—C6—H6B | 107.3 | O9'—Cl3'—O10' | 109.47 (6) |
C8—C7—N5 | 118.6 (4) | O12'—Cl3'—O10' | 109.47 (6) |
C8—C7—H7A | 107.7 | N4—Cu1—N5 | 173.04 (15) |
N5—C7—H7A | 107.7 | N4—Cu1—N3 | 91.33 (16) |
C8—C7—H7B | 107.7 | N5—Cu1—N3 | 89.92 (15) |
N5—C7—H7B | 107.7 | N4—Cu1—N1 | 89.65 (15) |
H7A—C7—H7B | 107.1 | N5—Cu1—N1 | 85.71 (14) |
C7—C8—C9 | 116.4 (4) | N3—Cu1—N1 | 148.41 (15) |
C7—C8—H8A | 108.2 | N4—Cu1—N2 | 90.22 (15) |
C9—C8—H8A | 108.2 | N5—Cu1—N2 | 96.19 (15) |
C7—C8—H8B | 108.2 | N3—Cu1—N2 | 102.67 (15) |
C9—C8—H8B | 108.2 | N1—Cu1—N2 | 108.90 (14) |
H8A—C8—H8B | 107.4 | C12—N1—C1 | 112.4 (4) |
N2—C9—C8 | 112.6 (4) | C12—N1—C11 | 109.0 (3) |
N2—C9—H9A | 109.1 | C1—N1—C11 | 109.4 (4) |
C8—C9—H9A | 109.1 | C12—N1—Cu1 | 108.6 (2) |
N2—C9—H9B | 109.1 | C1—N1—Cu1 | 111.0 (3) |
C8—C9—H9B | 109.1 | C11—N1—Cu1 | 106.2 (3) |
H9A—C9—H9B | 107.8 | C9—N2—Cu1 | 114.6 (3) |
C11—C10—N5 | 111.6 (4) | C9—N2—H2C | 108.6 |
C11—C10—H10A | 109.3 | Cu1—N2—H2C | 108.6 |
N5—C10—H10A | 109.3 | C9—N2—H2D | 108.6 |
C11—C10—H10B | 109.3 | Cu1—N2—H2D | 108.6 |
N5—C10—H10B | 109.3 | H2C—N2—H2D | 107.6 |
H10A—C10—H10B | 108.0 | C4—N3—Cu1 | 113.8 (3) |
C10—C11—N1 | 111.3 (4) | C4—N3—H3C | 108.8 |
C10—C11—H11A | 109.4 | Cu1—N3—H3C | 108.8 |
N1—C11—H11A | 109.4 | C4—N3—H3D | 108.8 |
C10—C11—H11B | 109.4 | Cu1—N3—H3D | 108.8 |
N1—C11—H11B | 109.4 | H3C—N3—H3D | 107.7 |
H11A—C11—H11B | 108.0 | C3—N4—Cu1 | 115.3 (3) |
N1—C12—C13 | 118.1 (3) | C3—N4—H4C | 108.5 |
N1—C12—H12A | 107.8 | Cu1—N4—H4C | 108.5 |
C13—C12—H12A | 107.8 | C3—N4—H4D | 108.5 |
N1—C12—H12B | 107.8 | Cu1—N4—H4D | 108.5 |
C13—C12—H12B | 107.8 | H4C—N4—H4D | 107.5 |
H12A—C12—H12B | 107.1 | C6—N5—C7 | 110.3 (3) |
C14—C13—C12 | 113.1 (4) | C6—N5—C10 | 108.7 (3) |
C14—C13—H13A | 109.0 | C7—N5—C10 | 107.4 (3) |
C12—C13—H13A | 109.0 | C6—N5—Cu1 | 110.6 (3) |
C14—C13—H13B | 109.0 | C7—N5—Cu1 | 115.3 (3) |
C12—C13—H13B | 109.0 | C10—N5—Cu1 | 104.2 (2) |
H13A—C13—H13B | 107.8 | C14—N6—H6C | 109.5 |
N6—C14—C13 | 113.2 (4) | C14—N6—H6D | 109.5 |
N6—C14—H14A | 108.9 | H6C—N6—H6D | 109.5 |
C13—C14—H14A | 108.9 | C14—N6—H6E | 109.5 |
N6—C14—H14B | 108.9 | H6C—N6—H6E | 109.5 |
C13—C14—H14B | 108.9 | H6D—N6—H6E | 109.5 |
| | | |
N1—C1—C2—C3 | −68.6 (5) | N4—Cu1—N2—C9 | 148.2 (3) |
C1—C2—C3—N4 | 65.6 (5) | N5—Cu1—N2—C9 | −34.6 (3) |
N3—C4—C5—C6 | −63.1 (5) | N3—Cu1—N2—C9 | 56.7 (3) |
C4—C5—C6—N5 | 64.1 (6) | N1—Cu1—N2—C9 | −122.1 (3) |
N5—C7—C8—C9 | 66.8 (6) | C5—C4—N3—Cu1 | 65.4 (4) |
C7—C8—C9—N2 | −72.2 (5) | N4—Cu1—N3—C4 | 117.3 (3) |
N5—C10—C11—N1 | 52.3 (5) | N5—Cu1—N3—C4 | −55.8 (3) |
N1—C12—C13—C14 | 157.8 (4) | N1—Cu1—N3—C4 | 25.8 (5) |
C12—C13—C14—N6 | 55.7 (5) | N2—Cu1—N3—C4 | −152.2 (3) |
C13—C12—N1—C1 | −55.0 (5) | C2—C3—N4—Cu1 | −64.3 (5) |
C13—C12—N1—C11 | 66.4 (5) | N3—Cu1—N4—C3 | −96.4 (3) |
C13—C12—N1—Cu1 | −178.3 (3) | N1—Cu1—N4—C3 | 52.1 (3) |
C2—C1—N1—C12 | −57.6 (5) | N2—Cu1—N4—C3 | 161.0 (3) |
C2—C1—N1—C11 | −178.9 (4) | C5—C6—N5—C7 | 66.6 (5) |
C2—C1—N1—Cu1 | 64.3 (4) | C5—C6—N5—C10 | −175.9 (4) |
C10—C11—N1—C12 | 84.6 (5) | C5—C6—N5—Cu1 | −62.1 (5) |
C10—C11—N1—C1 | −152.1 (4) | C8—C7—N5—C6 | −171.9 (4) |
C10—C11—N1—Cu1 | −32.2 (4) | C8—C7—N5—C10 | 69.9 (5) |
N4—Cu1—N1—C12 | 74.2 (3) | C8—C7—N5—Cu1 | −45.7 (5) |
N5—Cu1—N1—C12 | −111.0 (3) | C11—C10—N5—C6 | 74.8 (4) |
N3—Cu1—N1—C12 | 166.2 (3) | C11—C10—N5—C7 | −165.9 (4) |
N2—Cu1—N1—C12 | −15.9 (3) | C11—C10—N5—Cu1 | −43.1 (4) |
N4—Cu1—N1—C1 | −49.9 (3) | N3—Cu1—N5—C6 | 50.9 (3) |
N5—Cu1—N1—C1 | 124.9 (3) | N1—Cu1—N5—C6 | −97.8 (3) |
N3—Cu1—N1—C1 | 42.1 (4) | N2—Cu1—N5—C6 | 153.6 (3) |
N2—Cu1—N1—C1 | −140.0 (3) | N3—Cu1—N5—C7 | −75.1 (3) |
N4—Cu1—N1—C11 | −168.7 (3) | N1—Cu1—N5—C7 | 136.2 (3) |
N5—Cu1—N1—C11 | 6.1 (3) | N2—Cu1—N5—C7 | 27.6 (3) |
N3—Cu1—N1—C11 | −76.7 (4) | N3—Cu1—N5—C10 | 167.5 (3) |
N2—Cu1—N1—C11 | 101.2 (3) | N1—Cu1—N5—C10 | 18.8 (3) |
C8—C9—N2—Cu1 | 55.9 (4) | N2—Cu1—N5—C10 | −89.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O5i | 0.90 | 2.30 | 3.132 (5) | 153 |
N2—H2C···O5′i | 0.90 | 2.56 | 3.407 (18) | 158 |
N6—H6C···O5i | 0.89 | 2.51 | 3.064 (6) | 121 |
N6—H6E···O5′i | 0.89 | 2.47 | 2.906 (18) | 110 |
N3—H3C···O4ii | 0.90 | 2.38 | 3.246 (5) | 161 |
N3—H3C···O2′ii | 0.90 | 2.38 | 3.058 (12) | 132 |
N2—H2D···O10′iii | 0.90 | 2.16 | 2.961 (10) | 147 |
N2—H2D···O12iii | 0.90 | 2.44 | 3.317 (5) | 164 |
N3—H3D···O7iii | 0.90 | 2.11 | 2.979 (5) | 162 |
N3—H3D···O7′iii | 0.90 | 2.16 | 2.899 (13) | 139 |
N4—H4C···O7iii | 0.90 | 2.45 | 3.160 (5) | 136 |
N4—H4C···O12′iii | 0.90 | 2.52 | 3.310 (10) | 146 |
N4—H4C···O12iii | 0.90 | 2.57 | 3.152 (5) | 123 |
N4—H4D···O3′iii | 0.90 | 2.05 | 2.903 (13) | 158 |
N4—H4D···O2iii | 0.90 | 2.47 | 3.250 (5) | 146 |
N6—H6C···O1′iii | 0.89 | 1.96 | 2.775 (18) | 151 |
N6—H6C···O1iii | 0.89 | 2.25 | 3.103 (5) | 161 |
N6—H6D···O11′iv | 0.89 | 1.94 | 2.823 (10) | 169 |
N6—H6D···O10iv | 0.89 | 2.24 | 2.957 (5) | 138 |
N6—H6D···O9iv | 0.89 | 2.42 | 3.135 (5) | 138 |
N6—H6E···O6′ | 0.89 | 2.08 | 2.842 (15) | 143 |
N6—H6E···O6 | 0.89 | 2.14 | 2.919 (6) | 145 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+2. |