Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056267/bt2559sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056267/bt2559Isup2.hkl |
CCDC reference: 672608
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.007 Å
- R factor = 0.051
- wR factor = 0.132
- Data-to-parameter ratio = 38.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.92
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.03 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT213_ALERT_2_C Atom O5 has ADP max/min Ratio ............. 3.10 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.28 Ratio PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.42 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu2 - Cl2 .. 5.38 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (1) 1.03 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2 (1) 1.04
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The authors contributed to the work as follows. Habibi: superviser of Mokhtari for copper complex crystals, produced first version of manuscript; Montazerozohori: superviser of Lalegani for Schiff base synthesis; Lalegani: research student, prepared and crystallized the Schiff base; Mokhtari: graduate student, prepared and crystallized the copper complex; Harrington: collected data, dealt with twinning, solved and refined structure; Clegg: geometrical calculations, production of graphics and structure interpretation, extensively revised text and produced final version for submission. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
For related literature, see: Yamada (1999); Goswami & Eichhorn (1999); Rybak-Akimova et al. (1998); Amirnasr et al. (2005, 2006); Liu et al. (2005); Khalaji et al. (2007); Barron et al. (1988).
To a solution of 99 mg (1 mmol) CuCl in 5 ml acetonitrile a solution of 261 mg (1 mmol) of PPh3 in 5 ml acetonitrile was added. The mixture was stirred for 5 min and then 378 mg (1 mmol) of N,N'-bis(2-nitrocinnamaldehyde)ethylenediamine in 5 ml acetonitrile was added and the solution stirred for an additional 60 min. The volume of the solvent was reduced under vacuum to about 5 ml. The diffusion of diethyl ether vapour into the concentrated solution gave needle-like red crystals suitable for X-ray studies. The crystals were collected and dried in vacuo.
All H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C).
The crystal was found to be a non-merohedral twin, with symmetry-inequivalent reflections overlapping in the diffraction pattern, making it impossible to merge all equivalent reflections before the refinement. The deposited structure factors are in the format generated by the undocumented LIST 7 instruction of SHELXTL, in which the contributions of the twin components are identified following refinement of the twin fraction; this was 0.5095:0.4905 (6). The twin law (obtained as part of the cell and orientation matrix refinement and given to 3 decimal places) is: 1.009 0.019 0.013 / -0.059 0.999 0.030 / -0.140 - 0.098 0.986.
Data collection: GEMINI and SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
Fig. 1. The asymmetric unit, with atom labels and 40% probability displacement ellipsoids. H atoms have been omitted for clarity. |
[CuCl(C20H18N4O4)(C18H15P)] | Z = 4 |
Mr = 739.64 | F(000) = 1528 |
Triclinic, P1 | Dx = 1.392 Mg m−3 |
a = 8.4684 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.5749 (19) Å | Cell parameters from 6328 reflections |
c = 26.321 (3) Å | θ = 2.5–26.5° |
α = 100.338 (3)° | µ = 0.79 mm−1 |
β = 90.767 (3)° | T = 150 K |
γ = 103.499 (3)° | Rod, red |
V = 3528.2 (7) Å3 | 0.34 × 0.10 × 0.10 mm |
Bruker SMART 1K CCD diffractometer | 33770 independent reflections |
Radiation source: sealed tube | 21591 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
thin–slice ω scans | θmax = 28.4°, θmin = 1.4° |
Absorption correction: multi-scan (TWINABS; Bruker, 2005) | h = −11→11 |
Tmin = 0.753, Tmax = 0.901 | k = −22→21 |
56982 measured reflections | l = −34→35 |
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) = 0.132 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0326P)2 + 12.0057P] where P = (Fo2 + 2Fc2)/3 |
33770 reflections | (Δ/σ)max = 0.001 |
884 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
[CuCl(C20H18N4O4)(C18H15P)] | γ = 103.499 (3)° |
Mr = 739.64 | V = 3528.2 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.4684 (10) Å | Mo Kα radiation |
b = 16.5749 (19) Å | µ = 0.79 mm−1 |
c = 26.321 (3) Å | T = 150 K |
α = 100.338 (3)° | 0.34 × 0.10 × 0.10 mm |
β = 90.767 (3)° |
Bruker SMART 1K CCD diffractometer | 33770 independent reflections |
Absorption correction: multi-scan (TWINABS; Bruker, 2005) | 21591 reflections with I > 2σ(I) |
Tmin = 0.753, Tmax = 0.901 | Rint = 0.047 |
56982 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0326P)2 + 12.0057P] where P = (Fo2 + 2Fc2)/3 |
33770 reflections | Δρmax = 0.59 e Å−3 |
884 parameters | Δρmin = −0.53 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.83930 (6) | 0.34287 (3) | 0.286307 (18) | 0.02188 (11) | |
Cl1 | 0.75924 (14) | 0.43883 (7) | 0.35090 (4) | 0.0358 (3) | |
P1 | 0.64450 (12) | 0.24294 (6) | 0.24358 (4) | 0.0224 (2) | |
O1 | 1.0781 (5) | 0.3844 (3) | −0.03731 (13) | 0.0585 (10) | |
O2 | 1.1042 (4) | 0.3616 (3) | 0.03932 (13) | 0.0568 (10) | |
O3 | 1.1143 (5) | 0.1011 (2) | 0.45215 (13) | 0.0517 (9) | |
O4 | 1.0924 (5) | 0.0893 (3) | 0.53202 (13) | 0.0673 (12) | |
N1 | 1.0290 (4) | 0.3818 (2) | 0.00601 (13) | 0.0339 (8) | |
N2 | 1.0061 (4) | 0.42440 (19) | 0.24764 (11) | 0.0191 (6) | |
N3 | 1.0506 (4) | 0.3350 (2) | 0.32407 (12) | 0.0235 (7) | |
N4 | 1.0422 (6) | 0.1050 (2) | 0.49193 (15) | 0.0448 (10) | |
C1 | 0.8713 (5) | 0.4016 (2) | 0.01746 (15) | 0.0256 (9) | |
C2 | 0.7680 (6) | 0.3977 (3) | −0.02449 (16) | 0.0336 (10) | |
H2 | 0.8032 | 0.3880 | −0.0587 | 0.040* | |
C3 | 0.6144 (6) | 0.4082 (3) | −0.01604 (18) | 0.0409 (12) | |
H3 | 0.5425 | 0.4063 | −0.0445 | 0.049* | |
C4 | 0.5639 (5) | 0.4213 (3) | 0.03352 (18) | 0.0411 (12) | |
H4 | 0.4553 | 0.4256 | 0.0391 | 0.049* | |
C5 | 0.6702 (5) | 0.4284 (3) | 0.07542 (17) | 0.0346 (10) | |
H5 | 0.6345 | 0.4396 | 0.1095 | 0.042* | |
C6 | 0.8286 (5) | 0.4194 (3) | 0.06863 (15) | 0.0266 (9) | |
C7 | 0.9412 (5) | 0.4376 (2) | 0.11454 (14) | 0.0229 (8) | |
H7 | 1.0504 | 0.4668 | 0.1113 | 0.028* | |
C8 | 0.9034 (5) | 0.4169 (2) | 0.16037 (14) | 0.0226 (8) | |
H8 | 0.7985 | 0.3837 | 0.1648 | 0.027* | |
C9 | 1.0244 (4) | 0.4455 (2) | 0.20336 (14) | 0.0203 (8) | |
H9 | 1.1243 | 0.4826 | 0.1982 | 0.024* | |
C10 | 1.1457 (5) | 0.4580 (2) | 0.28535 (14) | 0.0226 (8) | |
H10A | 1.1164 | 0.4960 | 0.3153 | 0.027* | |
H10B | 1.2383 | 0.4907 | 0.2693 | 0.027* | |
C11 | 1.1923 (5) | 0.3841 (2) | 0.30284 (16) | 0.0254 (9) | |
H11A | 1.2282 | 0.3482 | 0.2732 | 0.030* | |
H11B | 1.2832 | 0.4049 | 0.3296 | 0.030* | |
C12 | 1.0730 (5) | 0.3071 (2) | 0.36506 (15) | 0.0240 (8) | |
H12 | 1.1806 | 0.3186 | 0.3799 | 0.029* | |
C13 | 0.9426 (5) | 0.2589 (2) | 0.38981 (15) | 0.0253 (9) | |
H13 | 0.8338 | 0.2496 | 0.3765 | 0.030* | |
C14 | 0.9718 (5) | 0.2269 (2) | 0.43105 (15) | 0.0280 (9) | |
H14 | 1.0824 | 0.2355 | 0.4425 | 0.034* | |
C15 | 0.8494 (5) | 0.1802 (3) | 0.46016 (15) | 0.0307 (10) | |
C16 | 0.6903 (6) | 0.1909 (3) | 0.46014 (18) | 0.0402 (11) | |
H16 | 0.6606 | 0.2265 | 0.4390 | 0.048* | |
C17 | 0.5754 (7) | 0.1512 (3) | 0.4900 (2) | 0.0514 (14) | |
H17 | 0.4680 | 0.1593 | 0.4889 | 0.062* | |
C18 | 0.6156 (8) | 0.0994 (3) | 0.5217 (2) | 0.0566 (16) | |
H18 | 0.5370 | 0.0735 | 0.5429 | 0.068* | |
C19 | 0.7692 (7) | 0.0860 (3) | 0.52203 (19) | 0.0513 (14) | |
H19 | 0.7975 | 0.0500 | 0.5431 | 0.062* | |
C20 | 0.8817 (6) | 0.1251 (3) | 0.49173 (16) | 0.0364 (11) | |
C21 | 0.5196 (4) | 0.2838 (2) | 0.20235 (16) | 0.0251 (9) | |
C22 | 0.5105 (4) | 0.3673 (2) | 0.21791 (15) | 0.0229 (8) | |
H22 | 0.5700 | 0.4004 | 0.2484 | 0.028* | |
C23 | 0.4149 (4) | 0.4027 (2) | 0.18919 (15) | 0.0249 (8) | |
H23 | 0.4096 | 0.4597 | 0.2001 | 0.030* | |
C24 | 0.3283 (5) | 0.3553 (3) | 0.14503 (17) | 0.0372 (11) | |
H24 | 0.2624 | 0.3794 | 0.1256 | 0.045* | |
C25 | 0.3372 (6) | 0.2727 (3) | 0.1291 (2) | 0.0568 (16) | |
H25 | 0.2769 | 0.2399 | 0.0986 | 0.068* | |
C26 | 0.4333 (6) | 0.2373 (3) | 0.1570 (2) | 0.0500 (14) | |
H26 | 0.4405 | 0.1807 | 0.1452 | 0.060* | |
C27 | 0.4928 (5) | 0.1833 (2) | 0.28019 (17) | 0.0306 (10) | |
C28 | 0.3288 (6) | 0.1827 (3) | 0.2772 (2) | 0.0466 (13) | |
H28 | 0.2898 | 0.2127 | 0.2542 | 0.056* | |
C29 | 0.2206 (7) | 0.1381 (3) | 0.3078 (3) | 0.068 (2) | |
H29 | 0.1086 | 0.1383 | 0.3056 | 0.082* | |
C30 | 0.2747 (8) | 0.0944 (3) | 0.3407 (2) | 0.0664 (19) | |
H30 | 0.2003 | 0.0641 | 0.3613 | 0.080* | |
C31 | 0.4375 (8) | 0.0938 (3) | 0.3442 (2) | 0.0561 (16) | |
H31 | 0.4752 | 0.0632 | 0.3671 | 0.067* | |
C32 | 0.5456 (6) | 0.1383 (3) | 0.31390 (17) | 0.0394 (11) | |
H32 | 0.6575 | 0.1379 | 0.3163 | 0.047* | |
C33 | 0.7079 (5) | 0.1586 (2) | 0.20031 (15) | 0.0250 (9) | |
C34 | 0.6046 (6) | 0.0798 (3) | 0.18249 (18) | 0.0379 (11) | |
H34 | 0.4959 | 0.0686 | 0.1930 | 0.045* | |
C35 | 0.6569 (7) | 0.0172 (3) | 0.14974 (17) | 0.0438 (12) | |
H35 | 0.5847 | −0.0365 | 0.1380 | 0.053* | |
C36 | 0.8133 (7) | 0.0332 (3) | 0.13436 (18) | 0.0480 (14) | |
H36 | 0.8496 | −0.0092 | 0.1116 | 0.058* | |
C37 | 0.9172 (6) | 0.1104 (4) | 0.1519 (2) | 0.0571 (16) | |
H37 | 1.0258 | 0.1210 | 0.1414 | 0.068* | |
C38 | 0.8655 (5) | 0.1734 (3) | 0.18492 (17) | 0.0373 (11) | |
H38 | 0.9388 | 0.2267 | 0.1969 | 0.045* | |
Cu2 | 0.48633 (6) | 0.68749 (3) | 0.219149 (18) | 0.02083 (11) | |
Cl2 | 0.33758 (12) | 0.58831 (6) | 0.15118 (4) | 0.0274 (2) | |
P2 | 0.38212 (12) | 0.79103 (6) | 0.25379 (4) | 0.0202 (2) | |
O5 | 0.9162 (6) | 0.9170 (3) | −0.04751 (15) | 0.0868 (16) | |
O6 | 0.9493 (5) | 0.8923 (2) | 0.02872 (15) | 0.0607 (10) | |
O7 | 0.7323 (4) | 0.6617 (3) | 0.47157 (14) | 0.0558 (10) | |
O8 | 0.6781 (5) | 0.5964 (2) | 0.53537 (13) | 0.0609 (11) | |
N5 | 0.8623 (6) | 0.8960 (3) | −0.00768 (16) | 0.0504 (12) | |
N6 | 0.7106 (4) | 0.7103 (2) | 0.18252 (12) | 0.0226 (7) | |
N7 | 0.6010 (4) | 0.61720 (19) | 0.25880 (11) | 0.0192 (6) | |
N8 | 0.6364 (5) | 0.6220 (3) | 0.49759 (14) | 0.0396 (9) | |
C39 | 0.6849 (6) | 0.8767 (3) | −0.00442 (16) | 0.0394 (11) | |
C40 | 0.5976 (9) | 0.9098 (3) | −0.0364 (2) | 0.0591 (16) | |
H40 | 0.6521 | 0.9428 | −0.0599 | 0.071* | |
C41 | 0.4332 (9) | 0.8953 (4) | −0.0344 (2) | 0.0669 (19) | |
H41 | 0.3727 | 0.9179 | −0.0565 | 0.080* | |
C42 | 0.3541 (7) | 0.8476 (4) | −0.0002 (2) | 0.0568 (15) | |
H42 | 0.2394 | 0.8381 | 0.0016 | 0.068* | |
C43 | 0.4423 (6) | 0.8134 (3) | 0.03156 (18) | 0.0402 (11) | |
H43 | 0.3865 | 0.7799 | 0.0545 | 0.048* | |
C44 | 0.6106 (6) | 0.8273 (3) | 0.03047 (15) | 0.0309 (10) | |
C45 | 0.6958 (5) | 0.7858 (3) | 0.06340 (16) | 0.0295 (9) | |
H45 | 0.7908 | 0.7699 | 0.0507 | 0.035* | |
C46 | 0.6514 (5) | 0.7686 (2) | 0.10935 (15) | 0.0258 (9) | |
H46 | 0.5569 | 0.7834 | 0.1233 | 0.031* | |
C47 | 0.7452 (5) | 0.7276 (2) | 0.13830 (15) | 0.0251 (9) | |
H47 | 0.8383 | 0.7128 | 0.1233 | 0.030* | |
C48 | 0.8224 (5) | 0.6720 (3) | 0.20750 (16) | 0.0270 (9) | |
H48A | 0.8813 | 0.7124 | 0.2379 | 0.032* | |
H48B | 0.9033 | 0.6570 | 0.1830 | 0.032* | |
C49 | 0.7239 (4) | 0.5931 (2) | 0.22429 (14) | 0.0226 (8) | |
H49A | 0.6702 | 0.5513 | 0.1937 | 0.027* | |
H49B | 0.7962 | 0.5672 | 0.2426 | 0.027* | |
C50 | 0.6007 (4) | 0.5961 (2) | 0.30332 (14) | 0.0204 (8) | |
H50 | 0.6753 | 0.5640 | 0.3101 | 0.024* | |
C51 | 0.4960 (4) | 0.6171 (2) | 0.34397 (14) | 0.0210 (8) | |
H51 | 0.4176 | 0.6479 | 0.3387 | 0.025* | |
C52 | 0.5109 (5) | 0.5926 (2) | 0.38895 (14) | 0.0231 (8) | |
H52 | 0.5981 | 0.5667 | 0.3929 | 0.028* | |
C53 | 0.4080 (5) | 0.6011 (2) | 0.43307 (15) | 0.0251 (9) | |
C54 | 0.2416 (5) | 0.5938 (3) | 0.42456 (17) | 0.0339 (10) | |
H54 | 0.1993 | 0.5913 | 0.3906 | 0.041* | |
C55 | 0.1368 (6) | 0.5901 (3) | 0.4644 (2) | 0.0442 (12) | |
H55 | 0.0248 | 0.5870 | 0.4577 | 0.053* | |
C56 | 0.1947 (7) | 0.5908 (3) | 0.51386 (18) | 0.0448 (13) | |
H56 | 0.1216 | 0.5852 | 0.5408 | 0.054* | |
C57 | 0.3585 (6) | 0.5997 (3) | 0.52404 (17) | 0.0396 (11) | |
H57 | 0.3997 | 0.6013 | 0.5581 | 0.047* | |
C58 | 0.4614 (5) | 0.6063 (3) | 0.48434 (15) | 0.0300 (9) | |
C59 | 0.5387 (5) | 0.8755 (2) | 0.29209 (16) | 0.0260 (9) | |
C60 | 0.5591 (5) | 0.8865 (3) | 0.34516 (17) | 0.0399 (11) | |
H60 | 0.4832 | 0.8530 | 0.3638 | 0.048* | |
C61 | 0.6920 (6) | 0.9472 (4) | 0.3714 (2) | 0.0571 (16) | |
H61 | 0.7036 | 0.9559 | 0.4081 | 0.068* | |
C62 | 0.8057 (6) | 0.9941 (4) | 0.3450 (2) | 0.0579 (16) | |
H62 | 0.8959 | 1.0349 | 0.3632 | 0.069* | |
C63 | 0.7883 (6) | 0.9819 (3) | 0.2919 (2) | 0.0516 (14) | |
H63 | 0.8668 | 1.0141 | 0.2733 | 0.062* | |
C64 | 0.6567 (5) | 0.9226 (3) | 0.26561 (19) | 0.0374 (11) | |
H64 | 0.6465 | 0.9139 | 0.2289 | 0.045* | |
C65 | 0.2164 (5) | 0.7695 (2) | 0.29703 (15) | 0.0237 (8) | |
C66 | 0.1528 (5) | 0.8326 (3) | 0.32549 (18) | 0.0387 (11) | |
H66 | 0.1985 | 0.8901 | 0.3237 | 0.046* | |
C67 | 0.0240 (6) | 0.8127 (3) | 0.35622 (19) | 0.0474 (13) | |
H67 | −0.0199 | 0.8561 | 0.3750 | 0.057* | |
C68 | −0.0414 (5) | 0.7288 (3) | 0.35961 (18) | 0.0414 (12) | |
H68 | −0.1272 | 0.7150 | 0.3818 | 0.050* | |
C69 | 0.0179 (5) | 0.6664 (3) | 0.33113 (18) | 0.0345 (10) | |
H69 | −0.0289 | 0.6091 | 0.3329 | 0.041* | |
C70 | 0.1455 (5) | 0.6858 (3) | 0.29972 (16) | 0.0273 (9) | |
H70 | 0.1851 | 0.6416 | 0.2799 | 0.033* | |
C71 | 0.2946 (4) | 0.8436 (2) | 0.20901 (15) | 0.0229 (8) | |
C72 | 0.2333 (5) | 0.7960 (3) | 0.16073 (15) | 0.0264 (9) | |
H72 | 0.2440 | 0.7395 | 0.1514 | 0.032* | |
C73 | 0.1567 (5) | 0.8307 (3) | 0.12622 (17) | 0.0355 (10) | |
H73 | 0.1157 | 0.7979 | 0.0933 | 0.043* | |
C74 | 0.1396 (5) | 0.9125 (3) | 0.1395 (2) | 0.0428 (12) | |
H74 | 0.0875 | 0.9362 | 0.1157 | 0.051* | |
C75 | 0.1982 (6) | 0.9595 (3) | 0.1873 (2) | 0.0437 (12) | |
H75 | 0.1853 | 1.0156 | 0.1965 | 0.052* | |
C76 | 0.2759 (5) | 0.9262 (3) | 0.22211 (18) | 0.0335 (10) | |
H76 | 0.3165 | 0.9595 | 0.2550 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0202 (2) | 0.0233 (2) | 0.0237 (2) | 0.00567 (19) | 0.00173 (19) | 0.0080 (2) |
Cl1 | 0.0520 (7) | 0.0422 (6) | 0.0244 (5) | 0.0289 (5) | 0.0130 (5) | 0.0118 (5) |
P1 | 0.0201 (5) | 0.0194 (5) | 0.0292 (5) | 0.0062 (4) | 0.0052 (4) | 0.0065 (4) |
O1 | 0.071 (3) | 0.086 (3) | 0.0298 (19) | 0.039 (2) | 0.0203 (18) | 0.0127 (19) |
O2 | 0.047 (2) | 0.105 (3) | 0.0319 (19) | 0.044 (2) | 0.0029 (16) | 0.015 (2) |
O3 | 0.074 (3) | 0.064 (2) | 0.0325 (19) | 0.032 (2) | 0.0181 (18) | 0.0263 (17) |
O4 | 0.114 (4) | 0.079 (3) | 0.0304 (19) | 0.054 (3) | 0.006 (2) | 0.0242 (19) |
N1 | 0.038 (2) | 0.040 (2) | 0.0225 (19) | 0.0122 (17) | 0.0043 (16) | 0.0006 (16) |
N2 | 0.0204 (16) | 0.0194 (16) | 0.0179 (16) | 0.0042 (13) | 0.0009 (13) | 0.0051 (13) |
N3 | 0.0242 (17) | 0.0225 (17) | 0.0256 (17) | 0.0077 (14) | 0.0021 (14) | 0.0062 (14) |
N4 | 0.075 (3) | 0.037 (2) | 0.030 (2) | 0.021 (2) | 0.005 (2) | 0.0156 (18) |
C1 | 0.029 (2) | 0.028 (2) | 0.0202 (19) | 0.0060 (17) | −0.0012 (17) | 0.0063 (17) |
C2 | 0.049 (3) | 0.032 (2) | 0.019 (2) | 0.008 (2) | −0.0046 (19) | 0.0050 (18) |
C3 | 0.042 (3) | 0.048 (3) | 0.032 (3) | 0.008 (2) | −0.018 (2) | 0.009 (2) |
C4 | 0.027 (2) | 0.055 (3) | 0.043 (3) | 0.009 (2) | −0.007 (2) | 0.015 (2) |
C5 | 0.026 (2) | 0.051 (3) | 0.029 (2) | 0.010 (2) | 0.0010 (18) | 0.011 (2) |
C6 | 0.025 (2) | 0.032 (2) | 0.024 (2) | 0.0051 (17) | 0.0009 (17) | 0.0097 (17) |
C7 | 0.0190 (19) | 0.030 (2) | 0.0208 (19) | 0.0049 (16) | 0.0016 (16) | 0.0073 (16) |
C8 | 0.0194 (19) | 0.029 (2) | 0.0203 (19) | 0.0056 (16) | 0.0045 (16) | 0.0085 (16) |
C9 | 0.0202 (19) | 0.0208 (19) | 0.0207 (19) | 0.0047 (15) | 0.0036 (15) | 0.0061 (15) |
C10 | 0.023 (2) | 0.023 (2) | 0.0200 (19) | 0.0009 (16) | −0.0012 (16) | 0.0051 (16) |
C11 | 0.020 (2) | 0.032 (2) | 0.027 (2) | 0.0070 (17) | 0.0005 (16) | 0.0129 (18) |
C12 | 0.028 (2) | 0.023 (2) | 0.022 (2) | 0.0068 (16) | −0.0039 (16) | 0.0066 (16) |
C13 | 0.028 (2) | 0.026 (2) | 0.023 (2) | 0.0060 (17) | 0.0007 (17) | 0.0066 (17) |
C14 | 0.034 (2) | 0.024 (2) | 0.025 (2) | 0.0043 (18) | −0.0008 (18) | 0.0061 (17) |
C15 | 0.042 (3) | 0.025 (2) | 0.021 (2) | 0.0008 (19) | 0.0024 (19) | 0.0033 (17) |
C16 | 0.044 (3) | 0.035 (3) | 0.037 (3) | 0.001 (2) | 0.005 (2) | 0.005 (2) |
C17 | 0.045 (3) | 0.053 (3) | 0.045 (3) | −0.005 (3) | 0.012 (2) | −0.001 (3) |
C18 | 0.073 (4) | 0.047 (3) | 0.036 (3) | −0.012 (3) | 0.025 (3) | 0.004 (2) |
C19 | 0.081 (4) | 0.039 (3) | 0.031 (3) | 0.004 (3) | 0.020 (3) | 0.014 (2) |
C20 | 0.059 (3) | 0.028 (2) | 0.020 (2) | 0.006 (2) | 0.005 (2) | 0.0061 (18) |
C21 | 0.0173 (19) | 0.025 (2) | 0.033 (2) | 0.0060 (16) | 0.0014 (17) | 0.0047 (17) |
C22 | 0.0156 (18) | 0.025 (2) | 0.027 (2) | 0.0010 (15) | 0.0039 (16) | 0.0069 (17) |
C23 | 0.020 (2) | 0.025 (2) | 0.032 (2) | 0.0073 (16) | 0.0054 (17) | 0.0097 (17) |
C24 | 0.029 (2) | 0.051 (3) | 0.035 (2) | 0.021 (2) | −0.003 (2) | 0.004 (2) |
C25 | 0.057 (3) | 0.058 (3) | 0.051 (3) | 0.029 (3) | −0.031 (3) | −0.020 (3) |
C26 | 0.053 (3) | 0.037 (3) | 0.056 (3) | 0.022 (2) | −0.024 (3) | −0.014 (2) |
C27 | 0.033 (2) | 0.0165 (19) | 0.039 (2) | 0.0021 (17) | 0.015 (2) | 0.0012 (18) |
C28 | 0.034 (3) | 0.025 (2) | 0.082 (4) | 0.007 (2) | 0.026 (3) | 0.010 (2) |
C29 | 0.047 (3) | 0.032 (3) | 0.123 (6) | 0.008 (2) | 0.054 (4) | 0.005 (3) |
C30 | 0.080 (5) | 0.033 (3) | 0.072 (4) | −0.006 (3) | 0.057 (4) | −0.003 (3) |
C31 | 0.083 (4) | 0.036 (3) | 0.036 (3) | −0.012 (3) | 0.013 (3) | 0.004 (2) |
C32 | 0.049 (3) | 0.032 (2) | 0.029 (2) | −0.006 (2) | 0.008 (2) | 0.0038 (19) |
C33 | 0.029 (2) | 0.026 (2) | 0.026 (2) | 0.0138 (17) | 0.0073 (17) | 0.0112 (17) |
C34 | 0.049 (3) | 0.024 (2) | 0.042 (3) | 0.009 (2) | 0.020 (2) | 0.008 (2) |
C35 | 0.078 (4) | 0.030 (2) | 0.031 (2) | 0.024 (3) | 0.012 (2) | 0.009 (2) |
C36 | 0.070 (4) | 0.058 (3) | 0.028 (2) | 0.047 (3) | 0.000 (2) | −0.003 (2) |
C37 | 0.036 (3) | 0.092 (5) | 0.046 (3) | 0.035 (3) | 0.008 (2) | −0.006 (3) |
C38 | 0.029 (2) | 0.050 (3) | 0.033 (2) | 0.014 (2) | 0.005 (2) | 0.003 (2) |
Cu2 | 0.0235 (2) | 0.0225 (2) | 0.0186 (2) | 0.00857 (19) | 0.00131 (19) | 0.00512 (19) |
Cl2 | 0.0316 (5) | 0.0251 (5) | 0.0226 (5) | −0.0003 (4) | −0.0066 (4) | 0.0066 (4) |
P2 | 0.0199 (5) | 0.0207 (5) | 0.0203 (5) | 0.0054 (4) | −0.0003 (4) | 0.0041 (4) |
O5 | 0.111 (4) | 0.091 (3) | 0.037 (2) | −0.025 (3) | 0.031 (2) | 0.019 (2) |
O6 | 0.058 (2) | 0.069 (3) | 0.051 (2) | −0.001 (2) | 0.018 (2) | 0.022 (2) |
O7 | 0.038 (2) | 0.084 (3) | 0.039 (2) | −0.0008 (19) | −0.0085 (16) | 0.019 (2) |
O8 | 0.084 (3) | 0.063 (2) | 0.039 (2) | 0.024 (2) | −0.026 (2) | 0.0117 (18) |
N5 | 0.076 (3) | 0.034 (2) | 0.032 (2) | −0.008 (2) | 0.023 (2) | 0.0073 (19) |
N6 | 0.0194 (16) | 0.0241 (17) | 0.0228 (17) | 0.0009 (13) | 0.0000 (13) | 0.0061 (14) |
N7 | 0.0200 (16) | 0.0194 (16) | 0.0183 (16) | 0.0040 (13) | 0.0025 (13) | 0.0047 (13) |
N8 | 0.050 (3) | 0.045 (2) | 0.0229 (19) | 0.014 (2) | −0.0131 (18) | 0.0021 (17) |
C39 | 0.069 (3) | 0.028 (2) | 0.020 (2) | 0.009 (2) | 0.008 (2) | 0.0053 (18) |
C40 | 0.115 (6) | 0.038 (3) | 0.030 (3) | 0.027 (3) | 0.005 (3) | 0.013 (2) |
C41 | 0.115 (6) | 0.064 (4) | 0.037 (3) | 0.051 (4) | −0.012 (3) | 0.012 (3) |
C42 | 0.069 (4) | 0.065 (4) | 0.047 (3) | 0.039 (3) | −0.008 (3) | 0.008 (3) |
C43 | 0.048 (3) | 0.043 (3) | 0.035 (3) | 0.018 (2) | 0.001 (2) | 0.012 (2) |
C44 | 0.049 (3) | 0.027 (2) | 0.018 (2) | 0.011 (2) | 0.0038 (19) | 0.0059 (17) |
C45 | 0.029 (2) | 0.029 (2) | 0.029 (2) | 0.0047 (18) | 0.0056 (18) | 0.0071 (18) |
C46 | 0.026 (2) | 0.028 (2) | 0.023 (2) | 0.0042 (17) | 0.0033 (17) | 0.0074 (17) |
C47 | 0.021 (2) | 0.029 (2) | 0.026 (2) | 0.0025 (16) | 0.0068 (17) | 0.0103 (17) |
C48 | 0.018 (2) | 0.036 (2) | 0.029 (2) | 0.0054 (17) | 0.0016 (17) | 0.0140 (19) |
C49 | 0.022 (2) | 0.028 (2) | 0.0200 (19) | 0.0099 (16) | 0.0035 (16) | 0.0064 (16) |
C50 | 0.0179 (19) | 0.0212 (19) | 0.0218 (19) | 0.0024 (15) | −0.0027 (15) | 0.0068 (15) |
C51 | 0.0203 (19) | 0.026 (2) | 0.0167 (18) | 0.0048 (16) | −0.0005 (15) | 0.0061 (15) |
C52 | 0.0197 (19) | 0.028 (2) | 0.0204 (19) | 0.0027 (16) | −0.0016 (15) | 0.0047 (16) |
C53 | 0.031 (2) | 0.026 (2) | 0.0178 (19) | 0.0068 (17) | 0.0010 (17) | 0.0039 (16) |
C54 | 0.033 (2) | 0.040 (3) | 0.028 (2) | 0.008 (2) | 0.0029 (19) | 0.0035 (19) |
C55 | 0.034 (3) | 0.047 (3) | 0.050 (3) | 0.007 (2) | 0.015 (2) | 0.006 (2) |
C56 | 0.063 (4) | 0.037 (3) | 0.033 (3) | 0.009 (2) | 0.028 (2) | 0.006 (2) |
C57 | 0.062 (3) | 0.035 (3) | 0.021 (2) | 0.011 (2) | 0.010 (2) | 0.0061 (19) |
C58 | 0.041 (3) | 0.028 (2) | 0.021 (2) | 0.0070 (19) | 0.0013 (18) | 0.0058 (17) |
C59 | 0.020 (2) | 0.024 (2) | 0.033 (2) | 0.0088 (16) | −0.0026 (17) | 0.0009 (17) |
C60 | 0.027 (2) | 0.058 (3) | 0.031 (2) | 0.009 (2) | −0.0029 (19) | −0.002 (2) |
C61 | 0.033 (3) | 0.083 (4) | 0.042 (3) | 0.013 (3) | −0.012 (2) | −0.021 (3) |
C62 | 0.021 (2) | 0.066 (4) | 0.067 (4) | 0.002 (2) | −0.006 (3) | −0.027 (3) |
C63 | 0.030 (3) | 0.048 (3) | 0.063 (4) | −0.005 (2) | 0.002 (2) | −0.007 (3) |
C64 | 0.030 (2) | 0.034 (2) | 0.043 (3) | −0.0004 (19) | 0.002 (2) | 0.003 (2) |
C65 | 0.021 (2) | 0.028 (2) | 0.023 (2) | 0.0056 (16) | −0.0009 (16) | 0.0049 (16) |
C66 | 0.034 (3) | 0.034 (3) | 0.041 (3) | 0.003 (2) | 0.010 (2) | −0.003 (2) |
C67 | 0.040 (3) | 0.059 (3) | 0.037 (3) | 0.011 (2) | 0.012 (2) | −0.006 (2) |
C68 | 0.023 (2) | 0.066 (3) | 0.033 (3) | 0.003 (2) | 0.0040 (19) | 0.012 (2) |
C69 | 0.021 (2) | 0.042 (3) | 0.044 (3) | 0.0036 (19) | −0.0019 (19) | 0.025 (2) |
C70 | 0.020 (2) | 0.031 (2) | 0.033 (2) | 0.0052 (17) | −0.0043 (17) | 0.0125 (18) |
C71 | 0.0150 (18) | 0.024 (2) | 0.032 (2) | 0.0053 (15) | 0.0015 (16) | 0.0096 (17) |
C72 | 0.025 (2) | 0.029 (2) | 0.028 (2) | 0.0074 (17) | 0.0019 (17) | 0.0107 (18) |
C73 | 0.026 (2) | 0.051 (3) | 0.033 (2) | 0.010 (2) | −0.0045 (19) | 0.013 (2) |
C74 | 0.030 (2) | 0.055 (3) | 0.056 (3) | 0.019 (2) | 0.002 (2) | 0.031 (3) |
C75 | 0.041 (3) | 0.036 (3) | 0.064 (3) | 0.019 (2) | 0.002 (3) | 0.022 (2) |
C76 | 0.029 (2) | 0.028 (2) | 0.045 (3) | 0.0078 (18) | −0.003 (2) | 0.008 (2) |
Cu1—Cl1 | 2.3332 (11) | Cu2—Cl2 | 2.3253 (11) |
Cu1—P1 | 2.1762 (11) | Cu2—P2 | 2.1730 (11) |
Cu1—N2 | 2.121 (3) | Cu2—N6 | 2.127 (3) |
Cu1—N3 | 2.077 (3) | Cu2—N7 | 2.080 (3) |
P1—C21 | 1.823 (4) | P2—C59 | 1.823 (4) |
P1—C27 | 1.827 (4) | P2—C65 | 1.829 (4) |
P1—C33 | 1.826 (4) | P2—C71 | 1.829 (4) |
O1—N1 | 1.223 (4) | O5—N5 | 1.224 (5) |
O2—N1 | 1.216 (4) | O6—N5 | 1.220 (5) |
O3—N4 | 1.218 (5) | O7—N8 | 1.220 (5) |
O4—N4 | 1.224 (5) | O8—N8 | 1.227 (5) |
N1—C1 | 1.470 (5) | N5—C39 | 1.468 (7) |
N2—C9 | 1.277 (5) | N6—C47 | 1.270 (5) |
N2—C10 | 1.468 (5) | N6—C48 | 1.465 (5) |
N3—C11 | 1.462 (5) | N7—C49 | 1.469 (5) |
N3—C12 | 1.277 (5) | N7—C50 | 1.282 (4) |
N4—C20 | 1.473 (6) | N8—C58 | 1.470 (6) |
C1—C2 | 1.382 (5) | C39—C40 | 1.377 (7) |
C1—C6 | 1.397 (5) | C39—C44 | 1.398 (6) |
C2—H2 | 0.950 | C40—H40 | 0.950 |
C2—C3 | 1.368 (6) | C40—C41 | 1.360 (9) |
C3—H3 | 0.950 | C41—H41 | 0.950 |
C3—C4 | 1.374 (7) | C41—C42 | 1.381 (8) |
C4—H4 | 0.950 | C42—H42 | 0.950 |
C4—C5 | 1.385 (6) | C42—C43 | 1.388 (6) |
C5—H5 | 0.950 | C43—H43 | 0.950 |
C5—C6 | 1.394 (6) | C43—C44 | 1.391 (6) |
C6—C7 | 1.471 (5) | C44—C45 | 1.475 (6) |
C7—H7 | 0.950 | C45—H45 | 0.950 |
C7—C8 | 1.336 (5) | C45—C46 | 1.331 (5) |
C8—H8 | 0.950 | C46—H46 | 0.950 |
C8—C9 | 1.451 (5) | C46—C47 | 1.447 (5) |
C9—H9 | 0.950 | C47—H47 | 0.950 |
C10—H10A | 0.990 | C48—H48A | 0.990 |
C10—H10B | 0.990 | C48—H48B | 0.990 |
C10—C11 | 1.514 (5) | C48—C49 | 1.520 (5) |
C11—H11A | 0.990 | C49—H49A | 0.990 |
C11—H11B | 0.990 | C49—H49B | 0.990 |
C12—H12 | 0.950 | C50—H50 | 0.950 |
C12—C13 | 1.440 (5) | C50—C51 | 1.445 (5) |
C13—H13 | 0.950 | C51—H51 | 0.950 |
C13—C14 | 1.334 (5) | C51—C52 | 1.332 (5) |
C14—H14 | 0.950 | C52—H52 | 0.950 |
C14—C15 | 1.456 (6) | C52—C53 | 1.467 (5) |
C15—C16 | 1.400 (6) | C53—C54 | 1.398 (6) |
C15—C20 | 1.407 (6) | C53—C58 | 1.399 (5) |
C16—H16 | 0.950 | C54—H54 | 0.950 |
C16—C17 | 1.381 (7) | C54—C55 | 1.383 (6) |
C17—H17 | 0.950 | C55—H55 | 0.950 |
C17—C18 | 1.390 (8) | C55—C56 | 1.382 (7) |
C18—H18 | 0.950 | C56—H56 | 0.950 |
C18—C19 | 1.370 (8) | C56—C57 | 1.378 (7) |
C19—H19 | 0.950 | C57—H57 | 0.950 |
C19—C20 | 1.371 (6) | C57—C58 | 1.373 (6) |
C21—C22 | 1.391 (5) | C59—C60 | 1.379 (6) |
C21—C26 | 1.390 (6) | C59—C64 | 1.395 (6) |
C22—H22 | 0.950 | C60—H60 | 0.950 |
C22—C23 | 1.390 (5) | C60—C61 | 1.398 (6) |
C23—H23 | 0.950 | C61—H61 | 0.950 |
C23—C24 | 1.373 (6) | C61—C62 | 1.371 (8) |
C24—H24 | 0.950 | C62—H62 | 0.950 |
C24—C25 | 1.377 (7) | C62—C63 | 1.376 (8) |
C25—H25 | 0.950 | C63—H63 | 0.950 |
C25—C26 | 1.383 (6) | C63—C64 | 1.382 (6) |
C26—H26 | 0.950 | C64—H64 | 0.950 |
C27—C28 | 1.388 (6) | C65—C66 | 1.392 (6) |
C27—C32 | 1.388 (6) | C65—C70 | 1.393 (5) |
C28—H28 | 0.950 | C66—H66 | 0.950 |
C28—C29 | 1.396 (7) | C66—C67 | 1.380 (6) |
C29—H29 | 0.950 | C67—H67 | 0.950 |
C29—C30 | 1.362 (9) | C67—C68 | 1.391 (7) |
C30—H30 | 0.950 | C68—H68 | 0.950 |
C30—C31 | 1.383 (8) | C68—C69 | 1.363 (6) |
C31—H31 | 0.950 | C69—H69 | 0.950 |
C31—C32 | 1.391 (6) | C69—C70 | 1.382 (6) |
C32—H32 | 0.950 | C70—H70 | 0.950 |
C33—C34 | 1.388 (6) | C71—C72 | 1.392 (5) |
C33—C38 | 1.379 (6) | C71—C76 | 1.397 (5) |
C34—H34 | 0.950 | C72—H72 | 0.950 |
C34—C35 | 1.385 (6) | C72—C73 | 1.386 (5) |
C35—H35 | 0.950 | C73—H73 | 0.950 |
C35—C36 | 1.370 (7) | C73—C74 | 1.381 (6) |
C36—H36 | 0.950 | C74—H74 | 0.950 |
C36—C37 | 1.369 (8) | C74—C75 | 1.373 (7) |
C37—H37 | 0.950 | C75—H75 | 0.950 |
C37—C38 | 1.391 (7) | C75—C76 | 1.383 (6) |
C38—H38 | 0.950 | C76—H76 | 0.950 |
Cl1—Cu1—P1 | 115.98 (5) | Cl2—Cu2—P2 | 117.85 (4) |
Cl1—Cu1—N2 | 101.81 (9) | Cl2—Cu2—N6 | 96.77 (9) |
Cl1—Cu1—N3 | 98.19 (9) | Cl2—Cu2—N7 | 104.00 (9) |
P1—Cu1—N2 | 121.16 (9) | P2—Cu2—N6 | 121.11 (9) |
P1—Cu1—N3 | 129.82 (9) | P2—Cu2—N7 | 126.11 (9) |
N2—Cu1—N3 | 82.70 (12) | N6—Cu2—N7 | 82.97 (12) |
Cu1—P1—C21 | 111.74 (13) | Cu2—P2—C59 | 110.15 (13) |
Cu1—P1—C27 | 118.29 (15) | Cu2—P2—C65 | 118.41 (13) |
Cu1—P1—C33 | 115.99 (14) | Cu2—P2—C71 | 116.39 (13) |
C21—P1—C27 | 102.3 (2) | C59—P2—C65 | 105.04 (18) |
C21—P1—C33 | 104.83 (18) | C59—P2—C71 | 104.04 (18) |
C27—P1—C33 | 101.88 (18) | C65—P2—C71 | 101.26 (17) |
O1—N1—O2 | 122.2 (4) | O5—N5—O6 | 122.8 (5) |
O1—N1—C1 | 118.6 (4) | O5—N5—C39 | 117.1 (5) |
O2—N1—C1 | 119.2 (3) | O6—N5—C39 | 120.1 (4) |
Cu1—N2—C9 | 140.3 (3) | Cu2—N6—C47 | 131.6 (3) |
Cu1—N2—C10 | 103.3 (2) | Cu2—N6—C48 | 108.0 (2) |
C9—N2—C10 | 116.1 (3) | C47—N6—C48 | 117.0 (3) |
Cu1—N3—C11 | 109.7 (2) | Cu2—N7—C49 | 104.9 (2) |
Cu1—N3—C12 | 131.3 (3) | Cu2—N7—C50 | 138.7 (3) |
C11—N3—C12 | 118.1 (3) | C49—N7—C50 | 116.2 (3) |
O3—N4—O4 | 123.6 (4) | O7—N8—O8 | 123.4 (4) |
O3—N4—C20 | 119.0 (4) | O7—N8—C58 | 118.6 (4) |
O4—N4—C20 | 117.4 (4) | O8—N8—C58 | 117.9 (4) |
N1—C1—C2 | 116.7 (4) | N5—C39—C40 | 117.3 (5) |
N1—C1—C6 | 120.2 (3) | N5—C39—C44 | 120.3 (4) |
C2—C1—C6 | 123.0 (4) | C40—C39—C44 | 122.4 (5) |
C1—C2—H2 | 120.5 | C39—C40—H40 | 120.1 |
C1—C2—C3 | 119.0 (4) | C39—C40—C41 | 119.8 (5) |
H2—C2—C3 | 120.5 | H40—C40—C41 | 120.1 |
C2—C3—H3 | 120.0 | C40—C41—H41 | 120.0 |
C2—C3—C4 | 120.1 (4) | C40—C41—C42 | 120.1 (5) |
H3—C3—C4 | 120.0 | H41—C41—C42 | 120.0 |
C3—C4—H4 | 119.8 | C41—C42—H42 | 120.0 |
C3—C4—C5 | 120.5 (4) | C41—C42—C43 | 119.9 (6) |
H4—C4—C5 | 119.8 | H42—C42—C43 | 120.0 |
C4—C5—H5 | 119.4 | C42—C43—H43 | 119.3 |
C4—C5—C6 | 121.3 (4) | C42—C43—C44 | 121.4 (5) |
H5—C5—C6 | 119.4 | H43—C43—C44 | 119.3 |
C1—C6—C5 | 116.0 (4) | C39—C44—C43 | 116.4 (4) |
C1—C6—C7 | 125.2 (4) | C39—C44—C45 | 124.9 (4) |
C5—C6—C7 | 118.5 (4) | C43—C44—C45 | 118.6 (4) |
C6—C7—H7 | 117.2 | C44—C45—H45 | 117.1 |
C6—C7—C8 | 125.7 (4) | C44—C45—C46 | 125.7 (4) |
H7—C7—C8 | 117.2 | H45—C45—C46 | 117.1 |
C7—C8—H8 | 120.4 | C45—C46—H46 | 119.6 |
C7—C8—C9 | 119.2 (4) | C45—C46—C47 | 120.8 (4) |
H8—C8—C9 | 120.4 | H46—C46—C47 | 119.6 |
N2—C9—C8 | 124.6 (4) | N6—C47—C46 | 124.0 (4) |
N2—C9—H9 | 117.7 | N6—C47—H47 | 118.0 |
C8—C9—H9 | 117.7 | C46—C47—H47 | 118.0 |
N2—C10—H10A | 110.1 | N6—C48—H48A | 110.0 |
N2—C10—H10B | 110.1 | N6—C48—H48B | 110.0 |
N2—C10—C11 | 108.0 (3) | N6—C48—C49 | 108.4 (3) |
H10A—C10—H10B | 108.4 | H48A—C48—H48B | 108.4 |
H10A—C10—C11 | 110.1 | H48A—C48—C49 | 110.0 |
H10B—C10—C11 | 110.1 | H48B—C48—C49 | 110.0 |
N3—C11—C10 | 108.6 (3) | N7—C49—C48 | 108.4 (3) |
N3—C11—H11A | 110.0 | N7—C49—H49A | 110.0 |
N3—C11—H11B | 110.0 | N7—C49—H49B | 110.0 |
C10—C11—H11A | 110.0 | C48—C49—H49A | 110.0 |
C10—C11—H11B | 110.0 | C48—C49—H49B | 110.0 |
H11A—C11—H11B | 108.4 | H49A—C49—H49B | 108.4 |
N3—C12—H12 | 118.5 | N7—C50—H50 | 117.3 |
N3—C12—C13 | 123.1 (4) | N7—C50—C51 | 125.3 (3) |
H12—C12—C13 | 118.5 | H50—C50—C51 | 117.3 |
C12—C13—H13 | 119.3 | C50—C51—H51 | 120.4 |
C12—C13—C14 | 121.3 (4) | C50—C51—C52 | 119.1 (4) |
H13—C13—C14 | 119.3 | H51—C51—C52 | 120.4 |
C13—C14—H14 | 117.0 | C51—C52—H52 | 116.3 |
C13—C14—C15 | 125.9 (4) | C51—C52—C53 | 127.4 (4) |
H14—C14—C15 | 117.0 | H52—C52—C53 | 116.3 |
C14—C15—C16 | 120.9 (4) | C52—C53—C54 | 119.9 (4) |
C14—C15—C20 | 123.8 (4) | C52—C53—C58 | 123.9 (4) |
C16—C15—C20 | 115.3 (4) | C54—C53—C58 | 115.7 (4) |
C15—C16—H16 | 119.2 | C53—C54—H54 | 119.2 |
C15—C16—C17 | 121.7 (5) | C53—C54—C55 | 121.7 (4) |
H16—C16—C17 | 119.2 | H54—C54—C55 | 119.2 |
C16—C17—H17 | 119.7 | C54—C55—H55 | 119.9 |
C16—C17—C18 | 120.5 (5) | C54—C55—C56 | 120.2 (5) |
H17—C17—C18 | 119.7 | H55—C55—C56 | 119.9 |
C17—C18—H18 | 120.2 | C55—C56—H56 | 120.1 |
C17—C18—C19 | 119.5 (5) | C55—C56—C57 | 119.9 (4) |
H18—C18—C19 | 120.2 | H56—C56—C57 | 120.1 |
C18—C19—H19 | 120.3 | C56—C57—H57 | 120.5 |
C18—C19—C20 | 119.4 (5) | C56—C57—C58 | 119.0 (4) |
H19—C19—C20 | 120.3 | H57—C57—C58 | 120.5 |
N4—C20—C15 | 119.6 (4) | N8—C58—C53 | 119.4 (4) |
N4—C20—C19 | 116.8 (4) | N8—C58—C57 | 117.2 (4) |
C15—C20—C19 | 123.6 (5) | C53—C58—C57 | 123.4 (4) |
P1—C21—C22 | 117.0 (3) | P2—C59—C60 | 123.0 (3) |
P1—C21—C26 | 124.5 (3) | P2—C59—C64 | 117.7 (3) |
C22—C21—C26 | 118.4 (4) | C60—C59—C64 | 118.6 (4) |
C21—C22—H22 | 119.7 | C59—C60—H60 | 120.1 |
C21—C22—C23 | 120.6 (4) | C59—C60—C61 | 119.8 (5) |
H22—C22—C23 | 119.7 | H60—C60—C61 | 120.1 |
C22—C23—H23 | 119.9 | C60—C61—H61 | 119.5 |
C22—C23—C24 | 120.2 (4) | C60—C61—C62 | 120.9 (5) |
H23—C23—C24 | 119.9 | H61—C61—C62 | 119.5 |
C23—C24—H24 | 120.1 | C61—C62—H62 | 120.2 |
C23—C24—C25 | 119.7 (4) | C61—C62—C63 | 119.6 (5) |
H24—C24—C25 | 120.1 | H62—C62—C63 | 120.2 |
C24—C25—H25 | 119.8 | C62—C63—H63 | 120.0 |
C24—C25—C26 | 120.5 (4) | C62—C63—C64 | 120.0 (5) |
H25—C25—C26 | 119.8 | H63—C63—C64 | 120.0 |
C21—C26—C25 | 120.5 (4) | C59—C64—C63 | 121.0 (5) |
C21—C26—H26 | 119.7 | C59—C64—H64 | 119.5 |
C25—C26—H26 | 119.7 | C63—C64—H64 | 119.5 |
P1—C27—C28 | 123.5 (4) | P2—C65—C66 | 123.1 (3) |
P1—C27—C32 | 118.1 (3) | P2—C65—C70 | 118.4 (3) |
C28—C27—C32 | 118.4 (4) | C66—C65—C70 | 118.4 (4) |
C27—C28—H28 | 119.8 | C65—C66—H66 | 119.6 |
C27—C28—C29 | 120.4 (5) | C65—C66—C67 | 120.7 (4) |
H28—C28—C29 | 119.8 | H66—C66—C67 | 119.6 |
C28—C29—H29 | 119.8 | C66—C67—H67 | 120.1 |
C28—C29—C30 | 120.4 (5) | C66—C67—C68 | 119.8 (5) |
H29—C29—C30 | 119.8 | H67—C67—C68 | 120.1 |
C29—C30—H30 | 119.8 | C67—C68—H68 | 120.0 |
C29—C30—C31 | 120.3 (5) | C67—C68—C69 | 119.9 (4) |
H30—C30—C31 | 119.8 | H68—C68—C69 | 120.0 |
C30—C31—H31 | 120.3 | C68—C69—H69 | 119.7 |
C30—C31—C32 | 119.4 (6) | C68—C69—C70 | 120.7 (4) |
H31—C31—C32 | 120.3 | H69—C69—C70 | 119.7 |
C27—C32—C31 | 121.1 (5) | C65—C70—C69 | 120.4 (4) |
C27—C32—H32 | 119.5 | C65—C70—H70 | 119.8 |
C31—C32—H32 | 119.5 | C69—C70—H70 | 119.8 |
P1—C33—C34 | 122.8 (3) | P2—C71—C72 | 117.5 (3) |
P1—C33—C38 | 118.7 (3) | P2—C71—C76 | 123.5 (3) |
C34—C33—C38 | 118.5 (4) | C72—C71—C76 | 118.8 (4) |
C33—C34—H34 | 119.4 | C71—C72—H72 | 119.8 |
C33—C34—C35 | 121.3 (5) | C71—C72—C73 | 120.3 (4) |
H34—C34—C35 | 119.4 | H72—C72—C73 | 119.8 |
C34—C35—H35 | 120.2 | C72—C73—H73 | 119.8 |
C34—C35—C36 | 119.6 (5) | C72—C73—C74 | 120.3 (4) |
H35—C35—C36 | 120.2 | H73—C73—C74 | 119.8 |
C35—C36—H36 | 120.1 | C73—C74—H74 | 120.2 |
C35—C36—C37 | 119.9 (4) | C73—C74—C75 | 119.7 (4) |
H36—C36—C37 | 120.1 | H74—C74—C75 | 120.2 |
C36—C37—H37 | 119.6 | C74—C75—H75 | 119.6 |
C36—C37—C38 | 120.8 (5) | C74—C75—C76 | 120.8 (4) |
H37—C37—C38 | 119.6 | H75—C75—C76 | 119.6 |
C33—C38—C37 | 120.0 (5) | C71—C76—C75 | 120.0 (4) |
C33—C38—H38 | 120.0 | C71—C76—H76 | 120.0 |
C37—C38—H38 | 120.0 | C75—C76—H76 | 120.0 |
Cl1—Cu1—P1—C21 | 69.27 (15) | Cl2—Cu2—P2—C59 | −163.61 (15) |
Cl1—Cu1—P1—C27 | −49.16 (16) | Cl2—Cu2—P2—C65 | 75.53 (15) |
Cl1—Cu1—P1—C33 | −170.66 (14) | Cl2—Cu2—P2—C71 | −45.55 (15) |
N2—Cu1—P1—C21 | −54.84 (17) | N6—Cu2—P2—C59 | −45.27 (18) |
N2—Cu1—P1—C27 | −173.26 (18) | N6—Cu2—P2—C65 | −166.13 (17) |
N2—Cu1—P1—C33 | 65.24 (17) | N6—Cu2—P2—C71 | 72.80 (17) |
N3—Cu1—P1—C21 | −162.95 (18) | N7—Cu2—P2—C59 | 59.99 (18) |
N3—Cu1—P1—C27 | 78.6 (2) | N7—Cu2—P2—C65 | −60.86 (18) |
N3—Cu1—P1—C33 | −42.88 (19) | N7—Cu2—P2—C71 | 178.06 (17) |
Cl1—Cu1—N2—C9 | −117.2 (4) | Cl2—Cu2—N6—C47 | 50.1 (4) |
Cl1—Cu1—N2—C10 | 70.1 (2) | Cl2—Cu2—N6—C48 | −108.1 (2) |
P1—Cu1—N2—C9 | 13.3 (4) | P2—Cu2—N6—C47 | −78.3 (4) |
P1—Cu1—N2—C10 | −159.42 (19) | P2—Cu2—N6—C48 | 123.5 (2) |
N3—Cu1—N2—C9 | 145.9 (4) | N7—Cu2—N6—C47 | 153.4 (4) |
N3—Cu1—N2—C10 | −26.8 (2) | N7—Cu2—N6—C48 | −4.8 (2) |
Cl1—Cu1—N3—C11 | −103.5 (2) | Cl2—Cu2—N7—C49 | 70.3 (2) |
Cl1—Cu1—N3—C12 | 64.8 (4) | Cl2—Cu2—N7—C50 | −115.7 (4) |
P1—Cu1—N3—C11 | 122.3 (2) | P2—Cu2—N7—C49 | −148.61 (19) |
P1—Cu1—N3—C12 | −69.4 (4) | P2—Cu2—N7—C50 | 25.4 (4) |
N2—Cu1—N3—C11 | −2.6 (2) | N6—Cu2—N7—C49 | −24.9 (2) |
N2—Cu1—N3—C12 | 165.7 (4) | N6—Cu2—N7—C50 | 149.1 (4) |
O1—N1—C1—C2 | 18.3 (6) | O5—N5—C39—C40 | −21.5 (6) |
O1—N1—C1—C6 | −164.6 (4) | O5—N5—C39—C44 | 159.1 (4) |
O2—N1—C1—C2 | −159.9 (4) | O6—N5—C39—C40 | 157.2 (5) |
O2—N1—C1—C6 | 17.2 (6) | O6—N5—C39—C44 | −22.1 (6) |
N1—C1—C2—C3 | 174.2 (4) | N5—C39—C40—C41 | −178.8 (5) |
C6—C1—C2—C3 | −2.8 (7) | C44—C39—C40—C41 | 0.5 (8) |
C1—C2—C3—C4 | −0.7 (7) | C39—C40—C41—C42 | 0.1 (8) |
C2—C3—C4—C5 | 3.3 (7) | C40—C41—C42—C43 | −0.9 (9) |
C3—C4—C5—C6 | −2.4 (7) | C41—C42—C43—C44 | 1.0 (8) |
C4—C5—C6—C1 | −1.0 (6) | C42—C43—C44—C39 | −0.4 (7) |
C4—C5—C6—C7 | 172.8 (4) | C42—C43—C44—C45 | −177.1 (4) |
N1—C1—C6—C5 | −173.3 (4) | N5—C39—C44—C43 | 178.9 (4) |
N1—C1—C6—C7 | 13.4 (6) | N5—C39—C44—C45 | −4.6 (6) |
C2—C1—C6—C5 | 3.6 (6) | C40—C39—C44—C43 | −0.4 (7) |
C2—C1—C6—C7 | −169.7 (4) | C40—C39—C44—C45 | 176.1 (4) |
C1—C6—C7—C8 | −146.7 (4) | C39—C44—C45—C46 | 151.1 (4) |
C5—C6—C7—C8 | 40.1 (6) | C43—C44—C45—C46 | −32.5 (6) |
C6—C7—C8—C9 | −174.8 (4) | C44—C45—C46—C47 | −179.9 (4) |
Cu1—N2—C9—C8 | 5.8 (6) | Cu2—N6—C47—C46 | 25.9 (6) |
C10—N2—C9—C8 | 177.9 (3) | C48—N6—C47—C46 | −177.5 (4) |
C7—C8—C9—N2 | −174.6 (4) | C45—C46—C47—N6 | 179.2 (4) |
Cu1—N2—C10—C11 | 51.4 (3) | Cu2—N6—C48—C49 | 33.0 (4) |
C9—N2—C10—C11 | −123.4 (3) | C47—N6—C48—C49 | −128.8 (4) |
Cu1—N3—C11—C10 | 31.3 (4) | Cu2—N7—C49—C48 | 50.5 (3) |
C12—N3—C11—C10 | −138.7 (3) | C50—N7—C49—C48 | −125.1 (3) |
N2—C10—C11—N3 | −57.1 (4) | N6—C48—C49—N7 | −57.3 (4) |
Cu1—N3—C12—C13 | 11.8 (6) | Cu2—N7—C50—C51 | 3.2 (6) |
C11—N3—C12—C13 | 179.3 (3) | C49—N7—C50—C51 | 176.8 (3) |
N3—C12—C13—C14 | 176.4 (4) | N7—C50—C51—C52 | −178.5 (4) |
C12—C13—C14—C15 | 177.6 (4) | C50—C51—C52—C53 | −174.3 (4) |
C13—C14—C15—C16 | −24.5 (6) | C51—C52—C53—C54 | 34.6 (6) |
C13—C14—C15—C20 | 158.6 (4) | C51—C52—C53—C58 | −153.5 (4) |
C14—C15—C16—C17 | −175.9 (4) | C52—C53—C54—C55 | 171.2 (4) |
C20—C15—C16—C17 | 1.2 (6) | C58—C53—C54—C55 | −1.4 (6) |
C15—C16—C17—C18 | 0.7 (7) | C53—C54—C55—C56 | −2.1 (7) |
C16—C17—C18—C19 | −1.9 (8) | C54—C55—C56—C57 | 3.4 (7) |
C17—C18—C19—C20 | 1.1 (8) | C55—C56—C57—C58 | −1.1 (7) |
C18—C19—C20—N4 | −177.2 (4) | C56—C57—C58—N8 | 175.7 (4) |
C18—C19—C20—C15 | 0.9 (7) | C56—C57—C58—C53 | −2.7 (7) |
C14—C15—C20—N4 | −6.9 (6) | C52—C53—C58—N8 | 13.3 (6) |
C14—C15—C20—C19 | 175.0 (4) | C52—C53—C58—C57 | −168.4 (4) |
C16—C15—C20—N4 | 176.0 (4) | C54—C53—C58—N8 | −174.5 (4) |
C16—C15—C20—C19 | −2.1 (6) | C54—C53—C58—C57 | 3.8 (6) |
O3—N4—C20—C15 | −33.6 (6) | O7—N8—C58—C53 | 28.6 (6) |
O3—N4—C20—C19 | 144.6 (5) | O7—N8—C58—C57 | −149.8 (4) |
O4—N4—C20—C15 | 149.7 (4) | O8—N8—C58—C53 | −153.6 (4) |
O4—N4—C20—C19 | −32.1 (6) | O8—N8—C58—C57 | 28.0 (6) |
Cu1—P1—C21—C22 | −27.4 (3) | Cu2—P2—C59—C60 | −99.6 (4) |
Cu1—P1—C21—C26 | 152.9 (4) | Cu2—P2—C59—C64 | 70.7 (3) |
C27—P1—C21—C22 | 100.1 (3) | C65—P2—C59—C60 | 28.9 (4) |
C27—P1—C21—C26 | −79.6 (4) | C65—P2—C59—C64 | −160.8 (3) |
C33—P1—C21—C22 | −153.9 (3) | C71—P2—C59—C60 | 134.9 (4) |
C33—P1—C21—C26 | 26.5 (5) | C71—P2—C59—C64 | −54.8 (4) |
P1—C21—C22—C23 | −178.6 (3) | P2—C59—C60—C61 | 173.4 (4) |
C26—C21—C22—C23 | 1.1 (6) | C64—C59—C60—C61 | 3.2 (7) |
C21—C22—C23—C24 | 0.0 (6) | C59—C60—C61—C62 | −2.2 (8) |
C22—C23—C24—C25 | −0.5 (7) | C60—C61—C62—C63 | 0.4 (8) |
C23—C24—C25—C26 | −0.3 (8) | C61—C62—C63—C64 | 0.1 (8) |
C24—C25—C26—C21 | 1.5 (9) | C62—C63—C64—C59 | 1.0 (8) |
P1—C21—C26—C25 | 177.8 (4) | P2—C59—C64—C63 | −173.4 (4) |
C22—C21—C26—C25 | −1.8 (8) | C60—C59—C64—C63 | −2.7 (7) |
Cu1—P1—C27—C28 | 117.3 (4) | Cu2—P2—C65—C66 | 173.0 (3) |
Cu1—P1—C27—C32 | −60.7 (4) | Cu2—P2—C65—C70 | −10.2 (3) |
C21—P1—C27—C28 | −5.9 (4) | C59—P2—C65—C66 | 49.5 (4) |
C21—P1—C27—C32 | 176.0 (3) | C59—P2—C65—C70 | −133.6 (3) |
C33—P1—C27—C28 | −114.2 (4) | C71—P2—C65—C66 | −58.5 (4) |
C33—P1—C27—C32 | 67.8 (4) | C71—P2—C65—C70 | 118.3 (3) |
P1—C27—C28—C29 | −177.6 (4) | P2—C65—C66—C67 | 177.8 (4) |
C32—C27—C28—C29 | 0.4 (7) | C70—C65—C66—C67 | 0.9 (7) |
C27—C28—C29—C30 | −0.4 (8) | C65—C66—C67—C68 | 1.2 (7) |
C28—C29—C30—C31 | 0.1 (9) | C66—C67—C68—C69 | −2.5 (7) |
C29—C30—C31—C32 | 0.1 (8) | C67—C68—C69—C70 | 1.6 (7) |
P1—C27—C32—C31 | 177.9 (4) | C68—C69—C70—C65 | 0.5 (6) |
C28—C27—C32—C31 | −0.3 (7) | P2—C65—C70—C69 | −178.8 (3) |
C30—C31—C32—C27 | 0.0 (7) | C66—C65—C70—C69 | −1.8 (6) |
Cu1—P1—C33—C34 | 160.3 (3) | Cu2—P2—C71—C72 | 28.3 (3) |
Cu1—P1—C33—C38 | −19.2 (4) | Cu2—P2—C71—C76 | −156.5 (3) |
C21—P1—C33—C34 | −75.9 (4) | C59—P2—C71—C72 | 149.6 (3) |
C21—P1—C33—C38 | 104.5 (3) | C59—P2—C71—C76 | −35.2 (4) |
C27—P1—C33—C34 | 30.4 (4) | C65—P2—C71—C72 | −101.6 (3) |
C27—P1—C33—C38 | −149.1 (3) | C65—P2—C71—C76 | 73.6 (4) |
P1—C33—C34—C35 | −179.9 (3) | P2—C71—C72—C73 | 176.1 (3) |
C38—C33—C34—C35 | −0.4 (7) | C76—C71—C72—C73 | 0.7 (6) |
C33—C34—C35—C36 | −0.3 (7) | C71—C72—C73—C74 | −0.4 (6) |
C34—C35—C36—C37 | 0.7 (7) | C72—C73—C74—C75 | −0.3 (7) |
C35—C36—C37—C38 | −0.5 (8) | C73—C74—C75—C76 | 0.7 (7) |
P1—C33—C38—C37 | −179.9 (4) | C74—C75—C76—C71 | −0.4 (7) |
C34—C33—C38—C37 | 0.6 (7) | P2—C71—C76—C75 | −175.5 (3) |
C36—C37—C38—C33 | −0.1 (8) | C72—C71—C76—C75 | −0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cl2i | 0.95 | 2.82 | 3.683 (4) | 151 |
C9—H9···Cl2i | 0.95 | 2.69 | 3.585 (4) | 158 |
C12—H12···O8ii | 0.95 | 2.53 | 3.263 (5) | 134 |
C24—H24···O2iii | 0.95 | 2.56 | 3.377 (5) | 145 |
C30—H30···O3iii | 0.95 | 2.52 | 3.245 (6) | 133 |
C37—H37···O5iv | 0.95 | 2.52 | 3.114 (6) | 121 |
C50—H50···Cl1 | 0.95 | 2.73 | 3.595 (4) | 153 |
C67—H67···O4v | 0.95 | 2.59 | 3.372 (6) | 140 |
C72—H72···Cl2 | 0.95 | 2.80 | 3.716 (4) | 163 |
C74—H74···O6iii | 0.95 | 2.46 | 3.237 (6) | 139 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z; (v) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [CuCl(C20H18N4O4)(C18H15P)] |
Mr | 739.64 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 8.4684 (10), 16.5749 (19), 26.321 (3) |
α, β, γ (°) | 100.338 (3), 90.767 (3), 103.499 (3) |
V (Å3) | 3528.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.79 |
Crystal size (mm) | 0.34 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD diffractometer |
Absorption correction | Multi-scan (TWINABS; Bruker, 2005) |
Tmin, Tmax | 0.753, 0.901 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 56982, 33770, 21591 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.132, 1.10 |
No. of reflections | 33770 |
No. of parameters | 884 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0326P)2 + 12.0057P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.59, −0.53 |
Computer programs: GEMINI and SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Bruker, 2005), SHELXTL and local programs.
Cu1—Cl1 | 2.3332 (11) | Cu2—Cl2 | 2.3253 (11) |
Cu1—P1 | 2.1762 (11) | Cu2—P2 | 2.1730 (11) |
Cu1—N2 | 2.121 (3) | Cu2—N6 | 2.127 (3) |
Cu1—N3 | 2.077 (3) | Cu2—N7 | 2.080 (3) |
Cl1—Cu1—P1 | 115.98 (5) | Cl2—Cu2—P2 | 117.85 (4) |
Cl1—Cu1—N2 | 101.81 (9) | Cl2—Cu2—N6 | 96.77 (9) |
Cl1—Cu1—N3 | 98.19 (9) | Cl2—Cu2—N7 | 104.00 (9) |
P1—Cu1—N2 | 121.16 (9) | P2—Cu2—N6 | 121.11 (9) |
P1—Cu1—N3 | 129.82 (9) | P2—Cu2—N7 | 126.11 (9) |
N2—Cu1—N3 | 82.70 (12) | N6—Cu2—N7 | 82.97 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cl2i | 0.95 | 2.82 | 3.683 (4) | 151 |
C9—H9···Cl2i | 0.95 | 2.69 | 3.585 (4) | 158 |
C12—H12···O8ii | 0.95 | 2.53 | 3.263 (5) | 134 |
C24—H24···O2iii | 0.95 | 2.56 | 3.377 (5) | 145 |
C30—H30···O3iii | 0.95 | 2.52 | 3.245 (6) | 133 |
C37—H37···O5iv | 0.95 | 2.52 | 3.114 (6) | 121 |
C50—H50···Cl1 | 0.95 | 2.73 | 3.595 (4) | 153 |
C67—H67···O4v | 0.95 | 2.59 | 3.372 (6) | 140 |
C72—H72···Cl2 | 0.95 | 2.80 | 3.716 (4) | 163 |
C74—H74···O6iii | 0.95 | 2.46 | 3.237 (6) | 139 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z; (v) −x+1, −y+1, −z+1. |
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Transition metal complexes containing Schiff base ligands have been of great interest for many years (Yamada, 1999). These complexes play an important role in coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Goswami & Eichhorn, 1999; Rybak-Akimova et al., 1998). The study of the variety of products in self-assembly processes between labile metal ions and flexible multidentate ligands is an interesting topic in supramolecular chemistry. The balance between the formation of different structures is often subtle. Factors that affect the coordination topology include not only the highly influential factors of metal and ligand coordination preferences, but also solvent-based influences, which have been extensively studied for silver(I) complexes (Amirnasr et al., 2006; Liu et al., 2005; Amirnasr et al., 2005; Khalaji et al., 2007). Here we report the results of the reaction of CuCl with N,N'-bis(2-nitrocinnamaldehyde)ethylenediamine and triphenylphosphine, which forms a copper(I) Schiff base complex, the crystal structure of which we have determined. The title complex is stable in dichloromethane for at least 24 h, but is decomposed in methanol much faster. A methanol solution exposed to the air slowly turns violet and finally green within 2 h. The complex is stable in air in the solid state for 2–3 weeks.
The asymmetric unit (Fig. 1) contains two complex molecules with essentially identical geometry. The bond lengths and angles around the Cu atoms are in good agreement with those found in similar copper(I) complexes (Barron et al., 1988). While a tetrahedral geometry is common for a four-coordinate copper(I) centre, the coordination in this complex is distorted by the restricted bite angle of the chelating ligand. The bond lengths in the chains of the ligand are consistent with extended electron delocalization.
The four nitro groups in the two independent molecules are twisted somewhat out of the planes of the benzene rings, with absolute O—N—C—C torsion angles in the range 17.2 (6)–33.6 (6)°. Dihedral angles between pairs of phenyl groups in the triphenylphosphine ligand are 82.44 (15), 77.02 (12) and 69.36 (14)° in one molecule, and 63.41 (15), 78.11 (12) and 70.67 (12)° in the other. Inspection shows that these rings form approximately a propeller arrangement in one molecule (angles between their normals and the P—Cu bond are 37.8, 65.4 and 72.6°), but a much less symmetrical arrangement in the other (corresponding angles are 20.3, 78.6 and 83.2°).
Molecules are linked via C—H···Cl and C—H···O interactions.