In the title copper(II) complex, dichloro[(
RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1
H-1,2,4-triazol-1-ylmethyl-κ
N4)pentan-3-ol]copper(II) ethanol tetrasolvate, [CuCl
2(C
16H
22ClN
3O)
4]·4C
2H
5OH, formed with the triazole fungicide tebuconazole, the Cu atom lies on an inversion center and has an elongated octahedral coordination. The molecules are linked to form a network
via O—H
Cl and O—H
O hydrogen bonds.
Supporting information
CCDC reference: 269550
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.051
- wR factor = 0.118
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.35
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 7023
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 7472
Completeness (_total/calc) 93.99%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.64 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C40
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C43
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C71
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
12 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
dichloro[(
RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1
H-1,2,4-triazol-1-ylmethyl-
κN4)pentan-3-ol]copper(II) ethanol tetrasolvate
top
Crystal data top
[CuCl2(C16H22ClN3O)4]·4C2H6O | Z = 1 |
Mr = 1549.98 | F(000) = 823.00 |
Triclinic, P1 | Dx = 1.263 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.7162 (1) Å | Cell parameters from 7526 reflections |
b = 14.3502 (2) Å | θ = 2.2–27.4° |
c = 15.8887 (1) Å | µ = 0.52 mm−1 |
α = 71.175 (3)° | T = 273 K |
β = 79.856 (3)° | Chunk, blue |
γ = 78.059 (1)° | 0.26 × 0.23 × 0.20 mm |
V = 2037.12 (5) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 7023 independent reflections |
Radiation source: rotation anode | 5140 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.4°, θmin = 2.3° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.864, Tmax = 0.901 | l = −19→19 |
15280 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0531P)2 + 0.9071P] where P = (Fo2 + 2Fc2)/3 |
7023 reflections | (Δ/σ)max = 0.001 |
465 parameters | Δρmax = 0.37 e Å−3 |
3 restraints | Δρmin = −0.33 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) |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.03829 (15) | |
Cl1 | 0.19339 (14) | 0.94469 (8) | −0.00449 (6) | 0.0929 (4) | |
Cl2 | 0.10710 (12) | 0.94129 (7) | 0.73364 (9) | 0.0916 (4) | |
Cl3 | 0.26646 (7) | 0.39299 (5) | 0.55509 (5) | 0.04698 (19) | |
O1 | −0.0851 (2) | 0.67221 (12) | 0.56382 (13) | 0.0404 (5) | |
H101 | −0.1330 | 0.6665 | 0.5287 | 0.061* | |
O2 | 0.2831 (2) | 0.30044 (14) | 0.85305 (15) | 0.0512 (5) | |
H201 | 0.2316 | 0.3466 | 0.8219 | 0.077* | |
O7 | 0.1195 (2) | 0.43371 (16) | 0.73114 (14) | 0.0518 (5) | |
H7 | 0.1461 | 0.4195 | 0.6842 | 0.078* | |
N1 | 0.3756 (2) | 0.62379 (16) | 0.52122 (15) | 0.0359 (5) | |
N2 | 0.2876 (2) | 0.78461 (17) | 0.50544 (18) | 0.0474 (6) | |
N3 | 0.1943 (2) | 0.72498 (16) | 0.55826 (15) | 0.0373 (5) | |
N4 | 0.5456 (2) | 0.45369 (16) | 0.62674 (15) | 0.0373 (5) | |
N5 | 0.6200 (3) | 0.4575 (2) | 0.75103 (18) | 0.0569 (7) | |
N6 | 0.5458 (2) | 0.38147 (17) | 0.76913 (16) | 0.0420 (6) | |
C1 | 0.2474 (3) | 0.62990 (19) | 0.56750 (18) | 0.0375 (6) | |
H1 | 0.2024 | 0.5760 | 0.6010 | 0.045* | |
C2 | 0.3937 (3) | 0.7200 (2) | 0.4848 (2) | 0.0465 (7) | |
H2 | 0.4751 | 0.7389 | 0.4480 | 0.056* | |
C3 | 0.0556 (3) | 0.7677 (2) | 0.5939 (2) | 0.0424 (7) | |
H3A | 0.0600 | 0.8344 | 0.5947 | 0.051* | |
H3B | 0.0341 | 0.7279 | 0.6554 | 0.051* | |
C4 | −0.0657 (3) | 0.77371 (18) | 0.54102 (18) | 0.0358 (6) | |
C5 | −0.0274 (3) | 0.81795 (19) | 0.43981 (18) | 0.0378 (6) | |
H5A | −0.1145 | 0.8495 | 0.4135 | 0.045* | |
H5B | 0.0285 | 0.8699 | 0.4305 | 0.045* | |
C6 | 0.0544 (3) | 0.7458 (2) | 0.38837 (18) | 0.0419 (7) | |
H6A | 0.1424 | 0.7139 | 0.4135 | 0.050* | |
H6B | −0.0011 | 0.6942 | 0.3956 | 0.050* | |
C7 | 0.0868 (3) | 0.79771 (19) | 0.29050 (18) | 0.0376 (6) | |
C8 | 0.0041 (3) | 0.7971 (2) | 0.2289 (2) | 0.0484 (7) | |
H8 | −0.0749 | 0.7653 | 0.2488 | 0.058* | |
C9 | 0.0347 (4) | 0.8421 (2) | 0.1388 (2) | 0.0578 (9) | |
H9 | −0.0219 | 0.8399 | 0.0982 | 0.069* | |
C10 | 0.1497 (4) | 0.8902 (2) | 0.1100 (2) | 0.0537 (8) | |
C11 | 0.2322 (3) | 0.8945 (2) | 0.1689 (2) | 0.0527 (8) | |
H11 | 0.3091 | 0.9285 | 0.1487 | 0.063* | |
C12 | 0.2011 (3) | 0.8480 (2) | 0.2587 (2) | 0.0479 (7) | |
H12 | 0.2582 | 0.8505 | 0.2989 | 0.057* | |
C13 | −0.2027 (3) | 0.8365 (2) | 0.5776 (2) | 0.0437 (7) | |
C14 | −0.3323 (3) | 0.8267 (3) | 0.5403 (2) | 0.0609 (9) | |
H14A | −0.3449 | 0.7580 | 0.5597 | 0.091* | |
H14B | −0.3183 | 0.8498 | 0.4761 | 0.091* | |
H14C | −0.4150 | 0.8660 | 0.5619 | 0.091* | |
C15 | −0.2286 (4) | 0.7979 (3) | 0.6795 (2) | 0.0642 (9) | |
H15A | −0.3197 | 0.8293 | 0.7000 | 0.096* | |
H15B | −0.1564 | 0.8131 | 0.7049 | 0.096* | |
H15C | −0.2259 | 0.7270 | 0.6978 | 0.096* | |
C16 | −0.1896 (3) | 0.9477 (2) | 0.5497 (2) | 0.0607 (9) | |
H16A | −0.2732 | 0.9837 | 0.5741 | 0.091* | |
H16B | −0.1791 | 0.9736 | 0.4856 | 0.091* | |
H16C | −0.1082 | 0.9551 | 0.5721 | 0.091* | |
C31 | 0.5016 (3) | 0.3809 (2) | 0.69513 (19) | 0.0426 (7) | |
H31 | 0.4477 | 0.3359 | 0.6918 | 0.051* | |
C32 | 0.6177 (3) | 0.4976 (2) | 0.6643 (2) | 0.0544 (8) | |
H32 | 0.6623 | 0.5519 | 0.6314 | 0.065* | |
C33 | 0.5165 (3) | 0.3205 (2) | 0.86108 (19) | 0.0468 (7) | |
H33A | 0.5751 | 0.3337 | 0.8980 | 0.056* | |
H33B | 0.5428 | 0.2507 | 0.8636 | 0.056* | |
C34 | 0.3607 (3) | 0.3391 (2) | 0.90011 (19) | 0.0422 (7) | |
C35 | 0.3035 (3) | 0.4508 (2) | 0.8798 (2) | 0.0453 (7) | |
H35A | 0.3053 | 0.4778 | 0.8153 | 0.054* | |
H35B | 0.2047 | 0.4570 | 0.9048 | 0.054* | |
C36 | 0.3705 (3) | 0.5194 (2) | 0.9101 (2) | 0.0553 (8) | |
H36A | 0.3520 | 0.5045 | 0.9747 | 0.066* | |
H36B | 0.4723 | 0.5086 | 0.8939 | 0.066* | |
C37 | 0.3103 (3) | 0.6270 (2) | 0.8665 (2) | 0.0507 (8) | |
C38 | 0.3558 (4) | 0.6766 (2) | 0.7798 (2) | 0.0596 (9) | |
H38 | 0.4290 | 0.6440 | 0.7482 | 0.072* | |
C39 | 0.2964 (4) | 0.7737 (3) | 0.7376 (3) | 0.0636 (9) | |
H39 | 0.3292 | 0.8061 | 0.6789 | 0.076* | |
C40 | 0.1886 (4) | 0.8205 (2) | 0.7846 (3) | 0.0585 (9) | |
C41 | 0.1422 (4) | 0.7745 (3) | 0.8703 (3) | 0.0684 (10) | |
H41 | 0.0694 | 0.8078 | 0.9016 | 0.082* | |
C42 | 0.2032 (4) | 0.6777 (3) | 0.9117 (3) | 0.0673 (10) | |
H42 | 0.1712 | 0.6466 | 0.9710 | 0.081* | |
C43 | 0.3412 (3) | 0.2754 (2) | 1.0006 (2) | 0.0517 (8) | |
C44 | 0.4399 (4) | 0.2914 (3) | 1.0572 (2) | 0.0767 (11) | |
H44A | 0.4338 | 0.3616 | 1.0479 | 0.115* | |
H44B | 0.5355 | 0.2638 | 1.0400 | 0.115* | |
H44C | 0.4129 | 0.2590 | 1.1192 | 0.115* | |
C45 | 0.3675 (5) | 0.1645 (3) | 1.0086 (3) | 0.0898 (13) | |
H45A | 0.4652 | 0.1445 | 0.9889 | 0.135* | |
H45B | 0.3085 | 0.1524 | 0.9719 | 0.135* | |
H45C | 0.3454 | 0.1268 | 1.0699 | 0.135* | |
C46 | 0.1885 (4) | 0.3018 (4) | 1.0407 (3) | 0.0947 (14) | |
H46A | 0.1714 | 0.2552 | 1.0989 | 0.142* | |
H46B | 0.1245 | 0.2989 | 1.0024 | 0.142* | |
H46C | 0.1739 | 0.3680 | 1.0461 | 0.142* | |
C71 | −0.0312 (3) | 0.4623 (2) | 0.7399 (2) | 0.0562 (8) | |
H71A | −0.0763 | 0.4059 | 0.7458 | 0.067* | |
H71B | −0.0591 | 0.5153 | 0.6870 | 0.067* | |
C72 | −0.0760 (4) | 0.4968 (4) | 0.8192 (3) | 0.1138 (19) | |
H72A | −0.0626 | 0.4413 | 0.8721 | 0.171* | |
H72B | −0.1743 | 0.5260 | 0.8203 | 0.171* | |
H72C | −0.0205 | 0.5457 | 0.8173 | 0.171* | |
O6A | 0.5683 (14) | 0.8488 (9) | 0.2206 (12) | 0.081 (3) | 0.50 |
H6A1 | 0.6285 | 0.8074 | 0.2036 | 0.121* | 0.50 |
C61A | 0.6346 (9) | 0.9068 (7) | 0.2536 (8) | 0.081 (3) | 0.50 |
H61A | 0.7205 | 0.9237 | 0.2149 | 0.097* | 0.50 |
H61B | 0.6591 | 0.8700 | 0.3133 | 0.097* | 0.50 |
C62A | 0.5305 (16) | 0.9998 (7) | 0.2553 (9) | 0.087 (3) | 0.50 |
H62A | 0.5335 | 1.0467 | 0.1965 | 0.131* | 0.50 |
H62B | 0.5548 | 1.0287 | 0.2964 | 0.131* | 0.50 |
H62C | 0.4369 | 0.9833 | 0.2743 | 0.131* | 0.50 |
O6B | 0.5826 (16) | 0.8352 (8) | 0.2439 (12) | 0.087 (3) | 0.50 |
H6B1 | 0.5857 | 0.8118 | 0.2980 | 0.131* | 0.50 |
C61B | 0.6110 (12) | 0.9344 (6) | 0.2152 (8) | 0.087 (3) | 0.50 |
H61C | 0.5768 | 0.9719 | 0.1581 | 0.105* | 0.50 |
H61D | 0.7113 | 0.9361 | 0.2110 | 0.105* | 0.50 |
C62B | 0.5262 (16) | 0.9731 (7) | 0.2915 (8) | 0.087 (3) | 0.50 |
H62D | 0.4271 | 0.9741 | 0.2915 | 0.131* | 0.50 |
H62E | 0.5428 | 1.0393 | 0.2830 | 0.131* | 0.50 |
H62F | 0.5557 | 0.9300 | 0.3476 | 0.131* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0371 (3) | 0.0388 (3) | 0.0369 (3) | 0.0054 (2) | −0.0059 (2) | −0.0147 (2) |
Cl1 | 0.1276 (9) | 0.0935 (7) | 0.0425 (5) | −0.0238 (7) | 0.0021 (5) | −0.0022 (5) |
Cl2 | 0.1034 (8) | 0.0479 (5) | 0.1269 (10) | 0.0036 (5) | −0.0480 (7) | −0.0223 (6) |
Cl3 | 0.0381 (4) | 0.0539 (4) | 0.0549 (5) | −0.0115 (3) | −0.0020 (3) | −0.0236 (4) |
O1 | 0.0468 (12) | 0.0301 (9) | 0.0437 (12) | −0.0057 (9) | −0.0080 (9) | −0.0093 (8) |
O2 | 0.0561 (13) | 0.0473 (11) | 0.0579 (14) | −0.0051 (10) | −0.0231 (10) | −0.0196 (11) |
O7 | 0.0432 (11) | 0.0631 (13) | 0.0510 (14) | −0.0063 (10) | −0.0078 (9) | −0.0200 (11) |
N1 | 0.0287 (11) | 0.0366 (12) | 0.0424 (14) | −0.0022 (10) | −0.0044 (10) | −0.0136 (10) |
N2 | 0.0374 (13) | 0.0345 (12) | 0.0738 (19) | −0.0065 (12) | −0.0073 (12) | −0.0198 (12) |
N3 | 0.0344 (12) | 0.0358 (12) | 0.0462 (14) | −0.0019 (11) | −0.0075 (10) | −0.0190 (11) |
N4 | 0.0347 (12) | 0.0417 (12) | 0.0361 (13) | −0.0033 (11) | −0.0043 (10) | −0.0141 (11) |
N5 | 0.0529 (16) | 0.0756 (18) | 0.0475 (17) | −0.0320 (15) | −0.0074 (12) | −0.0114 (14) |
N6 | 0.0367 (13) | 0.0454 (13) | 0.0421 (15) | −0.0055 (11) | −0.0073 (10) | −0.0098 (11) |
C1 | 0.0383 (15) | 0.0338 (14) | 0.0418 (16) | −0.0043 (13) | −0.0068 (12) | −0.0132 (12) |
C2 | 0.0367 (16) | 0.0416 (16) | 0.061 (2) | −0.0114 (14) | −0.0001 (14) | −0.0145 (14) |
C3 | 0.0385 (15) | 0.0437 (15) | 0.0500 (18) | 0.0022 (13) | −0.0040 (13) | −0.0267 (14) |
C4 | 0.0337 (14) | 0.0330 (13) | 0.0413 (16) | −0.0017 (12) | −0.0025 (11) | −0.0153 (12) |
C5 | 0.0352 (14) | 0.0313 (13) | 0.0445 (17) | −0.0025 (12) | −0.0042 (12) | −0.0102 (12) |
C6 | 0.0461 (16) | 0.0370 (14) | 0.0419 (17) | −0.0061 (13) | −0.0016 (13) | −0.0130 (13) |
C7 | 0.0392 (15) | 0.0316 (13) | 0.0402 (16) | −0.0006 (12) | −0.0031 (12) | −0.0121 (12) |
C8 | 0.0479 (17) | 0.0440 (16) | 0.055 (2) | −0.0139 (14) | −0.0074 (15) | −0.0124 (15) |
C9 | 0.071 (2) | 0.0578 (19) | 0.047 (2) | −0.0106 (18) | −0.0223 (17) | −0.0111 (16) |
C10 | 0.065 (2) | 0.0469 (17) | 0.0413 (19) | −0.0033 (17) | −0.0026 (15) | −0.0078 (14) |
C11 | 0.0470 (17) | 0.0532 (18) | 0.055 (2) | −0.0143 (15) | 0.0019 (15) | −0.0117 (16) |
C12 | 0.0446 (17) | 0.0518 (17) | 0.0483 (19) | −0.0102 (15) | −0.0064 (14) | −0.0142 (15) |
C13 | 0.0359 (15) | 0.0376 (15) | 0.0531 (19) | 0.0013 (13) | 0.0008 (13) | −0.0150 (13) |
C14 | 0.0356 (16) | 0.064 (2) | 0.079 (3) | 0.0054 (16) | −0.0039 (16) | −0.0259 (18) |
C15 | 0.056 (2) | 0.071 (2) | 0.056 (2) | 0.0051 (18) | 0.0098 (16) | −0.0242 (18) |
C16 | 0.054 (2) | 0.0398 (16) | 0.083 (3) | 0.0042 (15) | 0.0050 (17) | −0.0254 (17) |
C31 | 0.0433 (16) | 0.0461 (16) | 0.0408 (18) | −0.0089 (14) | −0.0055 (13) | −0.0150 (14) |
C32 | 0.0559 (19) | 0.062 (2) | 0.048 (2) | −0.0257 (17) | −0.0043 (15) | −0.0113 (16) |
C33 | 0.0445 (16) | 0.0490 (17) | 0.0406 (17) | −0.0025 (14) | −0.0117 (13) | −0.0043 (14) |
C34 | 0.0436 (16) | 0.0446 (16) | 0.0425 (17) | −0.0077 (14) | −0.0090 (13) | −0.0161 (13) |
C35 | 0.0437 (16) | 0.0481 (16) | 0.0497 (19) | −0.0064 (14) | −0.0111 (13) | −0.0197 (14) |
C36 | 0.060 (2) | 0.0537 (18) | 0.062 (2) | −0.0076 (16) | −0.0218 (16) | −0.0225 (16) |
C37 | 0.0508 (18) | 0.0470 (17) | 0.067 (2) | −0.0094 (15) | −0.0205 (16) | −0.0264 (16) |
C38 | 0.062 (2) | 0.058 (2) | 0.067 (2) | −0.0030 (17) | −0.0088 (17) | −0.0330 (18) |
C39 | 0.079 (2) | 0.0538 (19) | 0.063 (2) | −0.0110 (19) | −0.0151 (19) | −0.0216 (17) |
C40 | 0.059 (2) | 0.0435 (17) | 0.081 (3) | −0.0095 (17) | −0.0240 (19) | −0.0207 (18) |
C41 | 0.054 (2) | 0.053 (2) | 0.100 (3) | −0.0029 (18) | −0.002 (2) | −0.031 (2) |
C42 | 0.066 (2) | 0.064 (2) | 0.071 (3) | −0.0173 (19) | 0.0022 (19) | −0.0201 (19) |
C43 | 0.0574 (19) | 0.0583 (19) | 0.0408 (18) | −0.0204 (16) | −0.0056 (14) | −0.0100 (15) |
C44 | 0.099 (3) | 0.085 (3) | 0.051 (2) | −0.030 (2) | −0.031 (2) | −0.0058 (19) |
C45 | 0.143 (4) | 0.060 (2) | 0.060 (3) | −0.034 (2) | −0.021 (3) | 0.0067 (19) |
C46 | 0.073 (3) | 0.138 (4) | 0.059 (3) | −0.028 (3) | 0.008 (2) | −0.013 (3) |
C71 | 0.0475 (18) | 0.0563 (19) | 0.061 (2) | −0.0012 (16) | −0.0136 (15) | −0.0127 (16) |
C72 | 0.058 (2) | 0.197 (6) | 0.104 (4) | 0.014 (3) | −0.010 (2) | −0.089 (4) |
O6A | 0.073 (4) | 0.078 (5) | 0.112 (8) | −0.012 (3) | −0.019 (4) | −0.052 (5) |
C61A | 0.073 (4) | 0.078 (5) | 0.112 (8) | −0.012 (3) | −0.019 (4) | −0.052 (5) |
C62A | 0.086 (3) | 0.062 (3) | 0.117 (8) | −0.012 (3) | 0.004 (4) | −0.038 (4) |
O6B | 0.086 (3) | 0.062 (3) | 0.117 (8) | −0.012 (3) | 0.004 (4) | −0.038 (4) |
C61B | 0.086 (3) | 0.062 (3) | 0.117 (8) | −0.012 (3) | 0.004 (4) | −0.038 (4) |
C62B | 0.086 (3) | 0.062 (3) | 0.117 (8) | −0.012 (3) | 0.004 (4) | −0.038 (4) |
Geometric parameters (Å, º) top
Cu1—N4 | 2.006 (2) | C31—H31 | 0.9300 |
Cu1—N1 | 2.021 (2) | C32—H32 | 0.9300 |
Cl1—C10 | 1.746 (3) | C33—C34 | 1.535 (4) |
Cl2—C40 | 1.743 (3) | C33—H33A | 0.9700 |
O1—C4 | 1.427 (3) | C33—H33B | 0.9700 |
O1—H101 | 0.8200 | C34—C35 | 1.531 (4) |
O2—C34 | 1.440 (3) | C34—C43 | 1.563 (4) |
O2—H201 | 0.8200 | C35—C36 | 1.518 (4) |
O7—C71 | 1.431 (3) | C35—H35A | 0.9700 |
O7—H7 | 0.8200 | C35—H35B | 0.9700 |
N1—C1 | 1.332 (3) | C36—C37 | 1.512 (4) |
N1—C2 | 1.349 (4) | C36—H36A | 0.9700 |
N2—C2 | 1.308 (4) | C36—H36B | 0.9700 |
N2—N3 | 1.359 (3) | C37—C38 | 1.371 (5) |
N3—C1 | 1.325 (3) | C37—C42 | 1.375 (5) |
N3—C3 | 1.459 (3) | C38—C39 | 1.388 (5) |
N4—C31 | 1.320 (4) | C38—H38 | 0.9300 |
N4—C32 | 1.348 (4) | C39—C40 | 1.364 (5) |
N5—C32 | 1.314 (4) | C39—H39 | 0.9300 |
N5—N6 | 1.357 (3) | C40—C41 | 1.350 (5) |
N6—C31 | 1.324 (3) | C41—C42 | 1.386 (5) |
N6—C33 | 1.454 (4) | C41—H41 | 0.9300 |
C1—H1 | 0.9300 | C42—H42 | 0.9300 |
C2—H2 | 0.9300 | C43—C44 | 1.519 (4) |
C3—C4 | 1.537 (4) | C43—C45 | 1.527 (5) |
C3—H3A | 0.9700 | C43—C46 | 1.530 (5) |
C3—H3B | 0.9700 | C44—H44A | 0.9600 |
C4—C5 | 1.535 (4) | C44—H44B | 0.9600 |
C4—C13 | 1.579 (4) | C44—H44C | 0.9600 |
C5—C6 | 1.532 (3) | C45—H45A | 0.9600 |
C5—H5A | 0.9700 | C45—H45B | 0.9600 |
C5—H5B | 0.9700 | C45—H45C | 0.9600 |
C6—C7 | 1.500 (4) | C46—H46A | 0.9600 |
C6—H6A | 0.9700 | C46—H46B | 0.9600 |
C6—H6B | 0.9700 | C46—H46C | 0.9600 |
C7—C8 | 1.375 (4) | C71—C72 | 1.464 (5) |
C7—C12 | 1.381 (4) | C71—H71A | 0.9700 |
C8—C9 | 1.373 (4) | C71—H71B | 0.9700 |
C8—H8 | 0.9300 | C72—H72A | 0.9600 |
C9—C10 | 1.367 (5) | C72—H72B | 0.9600 |
C9—H9 | 0.9300 | C72—H72C | 0.9600 |
C10—C11 | 1.358 (5) | O6A—C61A | 1.416 (13) |
C11—C12 | 1.374 (4) | O6A—H6A1 | 0.8200 |
C11—H11 | 0.9300 | C61A—C62A | 1.503 (12) |
C12—H12 | 0.9300 | C61A—H61A | 0.9700 |
C13—C15 | 1.526 (4) | C61A—H61B | 0.9700 |
C13—C14 | 1.531 (4) | C62A—H62A | 0.9600 |
C13—C16 | 1.539 (4) | C62A—H62B | 0.9600 |
C14—H14A | 0.9600 | C62A—H62C | 0.9600 |
C14—H14B | 0.9600 | O6B—C61B | 1.418 (14) |
C14—H14C | 0.9600 | O6B—H6B1 | 0.8200 |
C15—H15A | 0.9600 | C61B—C62B | 1.532 (13) |
C15—H15B | 0.9600 | C61B—H61C | 0.9700 |
C15—H15C | 0.9600 | C61B—H61D | 0.9700 |
C16—H16A | 0.9600 | C62B—H62D | 0.9600 |
C16—H16B | 0.9600 | C62B—H62E | 0.9600 |
C16—H16C | 0.9600 | C62B—H62F | 0.9600 |
| | | |
N4—Cu1—N1 | 90.40 (9) | N6—C33—C34 | 113.6 (2) |
N4i—Cu1—N1 | 89.60 (9) | N6—C33—H33A | 108.9 |
N4i—Cu1—N1i | 90.40 (9) | C34—C33—H33A | 108.9 |
C4—O1—H101 | 109.5 | N6—C33—H33B | 108.9 |
C34—O2—H201 | 109.5 | C34—C33—H33B | 108.9 |
C71—O7—H7 | 109.5 | H33A—C33—H33B | 107.7 |
C1—N1—C2 | 103.3 (2) | O2—C34—C35 | 106.6 (2) |
C1—N1—Cu1 | 127.27 (18) | O2—C34—C33 | 105.8 (2) |
C2—N1—Cu1 | 129.02 (19) | C35—C34—C33 | 111.3 (2) |
C2—N2—N3 | 102.3 (2) | O2—C34—C43 | 106.3 (2) |
C1—N3—N2 | 110.5 (2) | C35—C34—C43 | 116.2 (2) |
C1—N3—C3 | 128.7 (2) | C33—C34—C43 | 109.9 (2) |
N2—N3—C3 | 120.8 (2) | C36—C35—C34 | 121.9 (2) |
C31—N4—C32 | 103.3 (2) | C36—C35—H35A | 106.9 |
C31—N4—Cu1 | 129.3 (2) | C34—C35—H35A | 106.9 |
C32—N4—Cu1 | 127.1 (2) | C36—C35—H35B | 106.9 |
C32—N5—N6 | 102.2 (2) | C34—C35—H35B | 106.9 |
C31—N6—N5 | 110.2 (2) | H35A—C35—H35B | 106.7 |
C31—N6—C33 | 129.9 (3) | C37—C36—C35 | 110.0 (2) |
N5—N6—C33 | 119.8 (2) | C37—C36—H36A | 109.7 |
N3—C1—N1 | 109.1 (2) | C35—C36—H36A | 109.7 |
N3—C1—H1 | 125.4 | C37—C36—H36B | 109.7 |
N1—C1—H1 | 125.4 | C35—C36—H36B | 109.7 |
N2—C2—N1 | 114.7 (3) | H36A—C36—H36B | 108.2 |
N2—C2—H2 | 122.6 | C38—C37—C42 | 117.4 (3) |
N1—C2—H2 | 122.6 | C38—C37—C36 | 121.8 (3) |
N3—C3—C4 | 114.3 (2) | C42—C37—C36 | 120.7 (3) |
N3—C3—H3A | 108.7 | C37—C38—C39 | 122.3 (3) |
C4—C3—H3A | 108.7 | C37—C38—H38 | 118.8 |
N3—C3—H3B | 108.7 | C39—C38—H38 | 118.8 |
C4—C3—H3B | 108.7 | C40—C39—C38 | 118.2 (4) |
H3A—C3—H3B | 107.6 | C40—C39—H39 | 120.9 |
O1—C4—C5 | 111.6 (2) | C38—C39—H39 | 120.9 |
O1—C4—C3 | 103.2 (2) | C41—C40—C39 | 121.1 (3) |
C5—C4—C3 | 111.9 (2) | C41—C40—Cl2 | 118.8 (3) |
O1—C4—C13 | 109.6 (2) | C39—C40—Cl2 | 120.0 (3) |
C5—C4—C13 | 111.7 (2) | C40—C41—C42 | 119.9 (3) |
C3—C4—C13 | 108.3 (2) | C40—C41—H41 | 120.0 |
C6—C5—C4 | 117.0 (2) | C42—C41—H41 | 120.0 |
C6—C5—H5A | 108.0 | C37—C42—C41 | 120.9 (4) |
C4—C5—H5A | 108.0 | C37—C42—H42 | 119.5 |
C6—C5—H5B | 108.0 | C41—C42—H42 | 119.5 |
C4—C5—H5B | 108.0 | C44—C43—C45 | 107.6 (3) |
H5A—C5—H5B | 107.3 | C44—C43—C46 | 108.3 (3) |
C7—C6—C5 | 112.1 (2) | C45—C43—C46 | 107.7 (3) |
C7—C6—H6A | 109.2 | C44—C43—C34 | 113.5 (3) |
C5—C6—H6A | 109.2 | C45—C43—C34 | 110.4 (3) |
C7—C6—H6B | 109.2 | C46—C43—C34 | 109.2 (3) |
C5—C6—H6B | 109.2 | C43—C44—H44A | 109.5 |
H6A—C6—H6B | 107.9 | C43—C44—H44B | 109.5 |
C8—C7—C12 | 117.3 (3) | H44A—C44—H44B | 109.5 |
C8—C7—C6 | 121.4 (3) | C43—C44—H44C | 109.5 |
C12—C7—C6 | 121.3 (3) | H44A—C44—H44C | 109.5 |
C9—C8—C7 | 122.0 (3) | H44B—C44—H44C | 109.5 |
C9—C8—H8 | 119.0 | C43—C45—H45A | 109.5 |
C7—C8—H8 | 119.0 | C43—C45—H45B | 109.5 |
C10—C9—C8 | 118.8 (3) | H45A—C45—H45B | 109.5 |
C10—C9—H9 | 120.6 | C43—C45—H45C | 109.5 |
C8—C9—H9 | 120.6 | H45A—C45—H45C | 109.5 |
C11—C10—C9 | 121.0 (3) | H45B—C45—H45C | 109.5 |
C11—C10—Cl1 | 119.5 (3) | C43—C46—H46A | 109.5 |
C9—C10—Cl1 | 119.5 (3) | C43—C46—H46B | 109.5 |
C10—C11—C12 | 119.4 (3) | H46A—C46—H46B | 109.5 |
C10—C11—H11 | 120.3 | C43—C46—H46C | 109.5 |
C12—C11—H11 | 120.3 | H46A—C46—H46C | 109.5 |
C11—C12—C7 | 121.4 (3) | H46B—C46—H46C | 109.5 |
C11—C12—H12 | 119.3 | O7—C71—C72 | 109.0 (3) |
C7—C12—H12 | 119.3 | O7—C71—H71A | 109.9 |
C15—C13—C14 | 107.8 (3) | C72—C71—H71A | 109.9 |
C15—C13—C16 | 108.9 (3) | O7—C71—H71B | 109.9 |
C14—C13—C16 | 108.4 (3) | C72—C71—H71B | 109.9 |
C15—C13—C4 | 110.5 (2) | H71A—C71—H71B | 108.3 |
C14—C13—C4 | 109.9 (2) | C71—C72—H72A | 109.5 |
C16—C13—C4 | 111.3 (2) | C71—C72—H72B | 109.5 |
C13—C14—H14A | 109.5 | H72A—C72—H72B | 109.5 |
C13—C14—H14B | 109.5 | C71—C72—H72C | 109.5 |
H14A—C14—H14B | 109.5 | H72A—C72—H72C | 109.5 |
C13—C14—H14C | 109.5 | H72B—C72—H72C | 109.5 |
H14A—C14—H14C | 109.5 | O6A—C61A—C62A | 106.9 (12) |
H14B—C14—H14C | 109.5 | O6A—C61A—H61A | 110.3 |
C13—C15—H15A | 109.5 | C62A—C61A—H61A | 110.3 |
C13—C15—H15B | 109.5 | O6A—C61A—H61B | 110.3 |
H15A—C15—H15B | 109.5 | C62A—C61A—H61B | 110.3 |
C13—C15—H15C | 109.5 | H61A—C61A—H61B | 108.6 |
H15A—C15—H15C | 109.5 | C61B—O6B—H6B1 | 109.5 |
H15B—C15—H15C | 109.5 | O6B—C61B—C62B | 100.6 (12) |
C13—C16—H16A | 109.5 | O6B—C61B—H61C | 111.6 |
C13—C16—H16B | 109.5 | C62B—C61B—H61C | 111.6 |
H16A—C16—H16B | 109.5 | O6B—C61B—H61D | 111.6 |
C13—C16—H16C | 109.5 | C62B—C61B—H61D | 111.6 |
H16A—C16—H16C | 109.5 | H61C—C61B—H61D | 109.4 |
H16B—C16—H16C | 109.5 | C61B—C62B—H62D | 109.5 |
N4—C31—N6 | 109.8 (3) | C61B—C62B—H62E | 109.5 |
N4—C31—H31 | 125.1 | H62D—C62B—H62E | 109.5 |
N6—C31—H31 | 125.1 | C61B—C62B—H62F | 109.5 |
N5—C32—N4 | 114.6 (3) | H62D—C62B—H62F | 109.5 |
N5—C32—H32 | 122.7 | H62E—C62B—H62F | 109.5 |
N4—C32—H32 | 122.7 | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H201···O7 | 0.82 | 1.91 | 2.715 (3) | 166 |
O7—H7···Cl3 | 0.82 | 2.28 | 3.083 (2) | 167 |
O1—H101···Cl3ii | 0.82 | 2.45 | 3.247 (2) | 166 |
O6A—H6A1···O2i | 0.82 | 2.00 | 2.790 (13) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |