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metal-organic compounds
The pyrimidine-2-mercaptan ligand in the title copper(I) chloride adduct, [CuCl(C4H4N2S)(C18H15P)2], coordinates to the metal atom through the doubly bonded S atom, the ligand being in the thione form. The coordination geometry of the Cu atom is tetrahedral.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011262/bt6455sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011262/bt6455Isup2.hkl |
CCDC reference: 242041
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - P1 .. 10.17 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.688 0.896 Tmin' and Tmax expected: 0.837 0.893 RR' = 0.820 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.67 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.84 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 8.44 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - S1 .. 6.67 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - P2 .. 7.98 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[CuCl(C4H4N2S)(C18H15P)2] | F(000) = 1520 |
Mr = 735.68 | Dx = 1.370 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4756 reflections |
a = 14.4631 (8) Å | θ = 2.3–24.3° |
b = 10.1438 (6) Å | µ = 0.87 mm−1 |
c = 24.393 (1) Å | T = 298 K |
β = 94.564 (1)° | Block, orange |
V = 3567.4 (3) Å3 | 0.20 × 0.19 × 0.13 mm |
Z = 4 |
Data collection top
Bruker SMART APEX area-detector diffractometer | 8258 independent reflections |
Radiation source: fine-focus sealed tube | 6403 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 28.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −18→18 |
Tmin = 0.688, Tmax = 0.896 | k = −6→12 |
21086 measured reflections | l = −32→32 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.562P] where P = (Fo2 + 2Fc2)/3 |
8067 reflections | (Δ/σ)max = 0.001 |
428 parameters | Δρmax = 0.64 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.765272 (19) | 0.30294 (3) | 0.357414 (11) | 0.03296 (10) | |
Cl1 | 0.73639 (4) | 0.53035 (6) | 0.34275 (3) | 0.04376 (16) | |
S1 | 0.91626 (5) | 0.27789 (7) | 0.40336 (3) | 0.04951 (18) | |
P1 | 0.67187 (4) | 0.21568 (6) | 0.41970 (2) | 0.03052 (14) | |
P2 | 0.75837 (4) | 0.23536 (6) | 0.26727 (2) | 0.02805 (13) | |
N1 | 0.93615 (16) | 0.5365 (2) | 0.39312 (10) | 0.0522 (6) | |
H1 | 0.8811 (10) | 0.531 (3) | 0.3775 (11) | 0.066 (9)* | |
N2 | 1.05699 (16) | 0.4258 (3) | 0.44241 (11) | 0.0648 (7) | |
C1 | 0.66271 (16) | 0.3125 (2) | 0.48259 (9) | 0.0346 (5) | |
C2 | 0.6539 (2) | 0.2576 (3) | 0.53358 (10) | 0.0552 (8) | |
H2 | 0.6618 | 0.1672 | 0.5384 | 0.066* | |
C3 | 0.6336 (3) | 0.3354 (3) | 0.57774 (11) | 0.0693 (10) | |
H3 | 0.6268 | 0.2971 | 0.6118 | 0.083* | |
C4 | 0.6235 (2) | 0.4684 (3) | 0.57107 (12) | 0.0669 (9) | |
H4 | 0.6102 | 0.5208 | 0.6007 | 0.080* | |
C5 | 0.6330 (3) | 0.5245 (3) | 0.52107 (13) | 0.0706 (10) | |
H5 | 0.6261 | 0.6151 | 0.5166 | 0.085* | |
C6 | 0.6529 (2) | 0.4462 (3) | 0.47691 (11) | 0.0523 (7) | |
H6 | 0.6597 | 0.4851 | 0.4429 | 0.063* | |
C7 | 0.71371 (18) | 0.0538 (2) | 0.44406 (9) | 0.0371 (5) | |
C8 | 0.7984 (2) | 0.0449 (3) | 0.47509 (11) | 0.0485 (6) | |
H8 | 0.8297 | 0.1215 | 0.4864 | 0.058* | |
C9 | 0.8365 (2) | −0.0768 (3) | 0.48930 (13) | 0.0635 (9) | |
H9 | 0.8926 | −0.0815 | 0.5107 | 0.076* | |
C10 | 0.7919 (3) | −0.1906 (3) | 0.47196 (14) | 0.0717 (10) | |
H10 | 0.8179 | −0.2722 | 0.4813 | 0.086* | |
C11 | 0.7092 (3) | −0.1834 (3) | 0.44082 (13) | 0.0680 (10) | |
H11 | 0.6791 | −0.2605 | 0.4289 | 0.082* | |
C12 | 0.6697 (2) | −0.0624 (3) | 0.42681 (11) | 0.0519 (7) | |
H12 | 0.6134 | −0.0590 | 0.4057 | 0.062* | |
C13 | 0.54825 (16) | 0.1913 (2) | 0.40016 (9) | 0.0329 (5) | |
C14 | 0.51130 (17) | 0.2385 (2) | 0.35011 (10) | 0.0392 (5) | |
H14 | 0.5501 | 0.2777 | 0.3262 | 0.047* | |
C15 | 0.41714 (19) | 0.2283 (3) | 0.33484 (11) | 0.0502 (7) | |
H15 | 0.3934 | 0.2607 | 0.3009 | 0.060* | |
C16 | 0.35886 (19) | 0.1705 (3) | 0.36966 (12) | 0.0520 (7) | |
H16 | 0.2958 | 0.1626 | 0.3592 | 0.062* | |
C17 | 0.39438 (19) | 0.1243 (3) | 0.42021 (12) | 0.0556 (7) | |
H17 | 0.3552 | 0.0859 | 0.4441 | 0.067* | |
C18 | 0.48787 (19) | 0.1350 (3) | 0.43536 (11) | 0.0496 (7) | |
H18 | 0.5111 | 0.1043 | 0.4696 | 0.059* | |
C19 | 0.82699 (15) | 0.3366 (2) | 0.22323 (9) | 0.0323 (5) | |
C20 | 0.91105 (17) | 0.3846 (3) | 0.24521 (11) | 0.0510 (7) | |
H20 | 0.9325 | 0.3622 | 0.2810 | 0.061* | |
C21 | 0.9641 (2) | 0.4661 (4) | 0.21437 (14) | 0.0699 (9) | |
H21 | 1.0206 | 0.4979 | 0.2298 | 0.084* | |
C22 | 0.9347 (2) | 0.5001 (3) | 0.16198 (13) | 0.0594 (8) | |
H22 | 0.9706 | 0.5546 | 0.1416 | 0.071* | |
C23 | 0.8515 (2) | 0.4531 (3) | 0.13972 (12) | 0.0560 (7) | |
H23 | 0.8307 | 0.4759 | 0.1039 | 0.067* | |
C24 | 0.79785 (18) | 0.3720 (3) | 0.16994 (10) | 0.0477 (6) | |
H24 | 0.7414 | 0.3408 | 0.1542 | 0.057* | |
C25 | 0.79159 (15) | 0.0659 (2) | 0.25369 (9) | 0.0322 (5) | |
C26 | 0.81515 (18) | 0.0208 (3) | 0.20278 (10) | 0.0439 (6) | |
H26 | 0.8197 | 0.0802 | 0.1741 | 0.053* | |
C27 | 0.8319 (2) | −0.1118 (3) | 0.19457 (13) | 0.0586 (8) | |
H27 | 0.8487 | −0.1409 | 0.1606 | 0.070* | |
C28 | 0.8237 (2) | −0.2004 (3) | 0.23658 (14) | 0.0595 (8) | |
H28 | 0.8338 | −0.2897 | 0.2308 | 0.071* | |
C29 | 0.80055 (19) | −0.1574 (3) | 0.28691 (13) | 0.0547 (7) | |
H29 | 0.7949 | −0.2176 | 0.3152 | 0.066* | |
C30 | 0.78565 (17) | −0.0248 (2) | 0.29578 (11) | 0.0432 (6) | |
H30 | 0.7715 | 0.0039 | 0.3303 | 0.052* | |
C31 | 0.64186 (15) | 0.2429 (2) | 0.23246 (8) | 0.0285 (4) | |
C32 | 0.59041 (15) | 0.1300 (2) | 0.21897 (9) | 0.0349 (5) | |
H32 | 0.6174 | 0.0475 | 0.2249 | 0.042* | |
C33 | 0.49969 (17) | 0.1389 (3) | 0.19681 (10) | 0.0424 (6) | |
H33 | 0.4659 | 0.0625 | 0.1885 | 0.051* | |
C34 | 0.45917 (17) | 0.2601 (3) | 0.18702 (10) | 0.0438 (6) | |
H34 | 0.3982 | 0.2659 | 0.1719 | 0.053* | |
C35 | 0.50959 (17) | 0.3737 (3) | 0.19986 (10) | 0.0422 (6) | |
H35 | 0.4825 | 0.4559 | 0.1930 | 0.051* | |
C36 | 0.59985 (16) | 0.3654 (2) | 0.22283 (9) | 0.0353 (5) | |
H36 | 0.6329 | 0.4421 | 0.2319 | 0.042* | |
C37 | 0.97278 (17) | 0.4214 (3) | 0.41361 (10) | 0.0444 (6) | |
C38 | 0.9803 (2) | 0.6526 (4) | 0.39901 (15) | 0.0735 (10) | |
H38 | 0.9529 | 0.7287 | 0.3840 | 0.088* | |
C39 | 1.0638 (3) | 0.6581 (4) | 0.42666 (16) | 0.0810 (11) | |
H39 | 1.0968 | 0.7366 | 0.4309 | 0.097* | |
C40 | 1.0985 (2) | 0.5410 (4) | 0.44857 (14) | 0.0772 (11) | |
H40 | 1.1553 | 0.5437 | 0.4692 | 0.093* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03839 (17) | 0.02878 (16) | 0.03160 (16) | −0.00209 (12) | 0.00215 (12) | 0.00000 (11) |
Cl1 | 0.0440 (3) | 0.0282 (3) | 0.0580 (4) | 0.0033 (3) | −0.0026 (3) | 0.0057 (3) |
S1 | 0.0399 (4) | 0.0430 (4) | 0.0635 (4) | 0.0025 (3) | −0.0090 (3) | 0.0045 (3) |
P1 | 0.0407 (3) | 0.0248 (3) | 0.0262 (3) | −0.0018 (2) | 0.0034 (2) | −0.0006 (2) |
P2 | 0.0290 (3) | 0.0271 (3) | 0.0281 (3) | −0.0011 (2) | 0.0028 (2) | 0.0018 (2) |
N1 | 0.0414 (13) | 0.0492 (15) | 0.0640 (15) | −0.0079 (11) | −0.0076 (11) | −0.0008 (12) |
N2 | 0.0404 (13) | 0.083 (2) | 0.0682 (17) | −0.0116 (13) | −0.0145 (12) | 0.0069 (14) |
C1 | 0.0415 (13) | 0.0316 (13) | 0.0306 (11) | −0.0011 (10) | 0.0031 (10) | −0.0059 (9) |
C2 | 0.089 (2) | 0.0435 (16) | 0.0333 (13) | 0.0191 (15) | 0.0070 (14) | 0.0001 (12) |
C3 | 0.108 (3) | 0.070 (2) | 0.0300 (14) | 0.029 (2) | 0.0086 (15) | −0.0033 (14) |
C4 | 0.093 (2) | 0.060 (2) | 0.0495 (18) | 0.0112 (18) | 0.0144 (16) | −0.0225 (15) |
C5 | 0.114 (3) | 0.0345 (16) | 0.066 (2) | 0.0051 (17) | 0.0256 (19) | −0.0149 (15) |
C6 | 0.082 (2) | 0.0318 (14) | 0.0449 (15) | −0.0011 (13) | 0.0190 (14) | −0.0015 (11) |
C7 | 0.0574 (15) | 0.0285 (12) | 0.0263 (11) | 0.0029 (11) | 0.0098 (10) | 0.0021 (9) |
C8 | 0.0574 (17) | 0.0445 (16) | 0.0437 (15) | 0.0082 (13) | 0.0044 (12) | 0.0017 (12) |
C9 | 0.072 (2) | 0.064 (2) | 0.0559 (18) | 0.0273 (17) | 0.0102 (15) | 0.0114 (15) |
C10 | 0.116 (3) | 0.0450 (19) | 0.0561 (19) | 0.0327 (19) | 0.017 (2) | 0.0129 (15) |
C11 | 0.123 (3) | 0.0283 (15) | 0.0537 (18) | 0.0039 (17) | 0.0132 (19) | 0.0002 (13) |
C12 | 0.086 (2) | 0.0300 (14) | 0.0391 (14) | −0.0024 (13) | 0.0030 (14) | 0.0004 (11) |
C13 | 0.0413 (13) | 0.0270 (12) | 0.0309 (11) | −0.0043 (9) | 0.0059 (10) | −0.0039 (9) |
C14 | 0.0463 (14) | 0.0381 (14) | 0.0342 (12) | 0.0019 (11) | 0.0106 (10) | 0.0013 (10) |
C15 | 0.0502 (16) | 0.0567 (18) | 0.0431 (15) | 0.0090 (13) | −0.0005 (12) | 0.0014 (13) |
C16 | 0.0399 (14) | 0.0495 (17) | 0.0664 (19) | −0.0031 (12) | 0.0025 (13) | −0.0085 (14) |
C17 | 0.0484 (16) | 0.0539 (18) | 0.0658 (19) | −0.0147 (14) | 0.0131 (14) | 0.0087 (15) |
C18 | 0.0555 (16) | 0.0521 (17) | 0.0413 (14) | −0.0121 (13) | 0.0060 (12) | 0.0131 (12) |
C19 | 0.0325 (11) | 0.0290 (12) | 0.0365 (12) | −0.0012 (9) | 0.0100 (9) | 0.0023 (9) |
C20 | 0.0348 (13) | 0.0652 (19) | 0.0525 (16) | −0.0092 (13) | 0.0001 (12) | 0.0110 (14) |
C21 | 0.0348 (15) | 0.087 (2) | 0.088 (2) | −0.0207 (16) | 0.0071 (15) | 0.014 (2) |
C22 | 0.0539 (18) | 0.0523 (18) | 0.076 (2) | −0.0052 (14) | 0.0282 (16) | 0.0202 (15) |
C23 | 0.0592 (18) | 0.0633 (19) | 0.0475 (16) | −0.0013 (15) | 0.0170 (13) | 0.0199 (14) |
C24 | 0.0459 (15) | 0.0584 (18) | 0.0391 (14) | −0.0119 (13) | 0.0045 (11) | 0.0066 (12) |
C25 | 0.0286 (11) | 0.0304 (12) | 0.0375 (12) | −0.0002 (9) | 0.0020 (9) | 0.0009 (9) |
C26 | 0.0511 (15) | 0.0412 (15) | 0.0399 (14) | 0.0026 (12) | 0.0073 (11) | −0.0036 (11) |
C27 | 0.0652 (19) | 0.0503 (18) | 0.0609 (18) | 0.0067 (15) | 0.0081 (15) | −0.0195 (15) |
C28 | 0.0587 (18) | 0.0334 (15) | 0.086 (2) | 0.0063 (13) | 0.0009 (16) | −0.0097 (15) |
C29 | 0.0548 (17) | 0.0338 (15) | 0.076 (2) | 0.0037 (12) | 0.0079 (15) | 0.0125 (14) |
C30 | 0.0459 (14) | 0.0359 (14) | 0.0490 (15) | 0.0054 (11) | 0.0112 (12) | 0.0072 (11) |
C31 | 0.0309 (11) | 0.0312 (12) | 0.0238 (10) | −0.0015 (9) | 0.0051 (8) | 0.0016 (9) |
C32 | 0.0335 (12) | 0.0316 (12) | 0.0399 (13) | −0.0024 (10) | 0.0037 (10) | 0.0042 (10) |
C33 | 0.0370 (13) | 0.0449 (15) | 0.0450 (14) | −0.0095 (11) | 0.0006 (11) | 0.0041 (12) |
C34 | 0.0325 (12) | 0.0553 (17) | 0.0429 (14) | 0.0010 (12) | −0.0015 (10) | 0.0092 (12) |
C35 | 0.0434 (14) | 0.0417 (15) | 0.0409 (13) | 0.0113 (12) | −0.0002 (11) | 0.0049 (11) |
C36 | 0.0408 (13) | 0.0309 (12) | 0.0338 (12) | 0.0008 (10) | 0.0008 (10) | −0.0016 (10) |
C37 | 0.0352 (13) | 0.0578 (17) | 0.0398 (14) | −0.0012 (12) | 0.0010 (11) | 0.0007 (12) |
C38 | 0.073 (2) | 0.054 (2) | 0.091 (3) | −0.0200 (17) | −0.0052 (19) | −0.0030 (18) |
C39 | 0.072 (2) | 0.080 (3) | 0.088 (3) | −0.039 (2) | −0.008 (2) | −0.004 (2) |
C40 | 0.0476 (18) | 0.113 (3) | 0.068 (2) | −0.025 (2) | −0.0115 (16) | 0.000 (2) |
Geometric parameters (Å, º) top
Cu1—P1 | 2.2899 (6) | C16—C17 | 1.379 (4) |
Cu1—P2 | 2.2978 (6) | C16—H16 | 0.9300 |
Cu1—S1 | 2.3875 (7) | C17—C18 | 1.377 (4) |
Cu1—Cl1 | 2.3664 (7) | C17—H17 | 0.9300 |
S1—C37 | 1.679 (3) | C18—H18 | 0.9300 |
P1—C13 | 1.830 (2) | C19—C20 | 1.378 (3) |
P1—C7 | 1.833 (2) | C19—C24 | 1.382 (3) |
P1—C1 | 1.835 (2) | C20—C21 | 1.389 (4) |
P2—C25 | 1.823 (2) | C20—H20 | 0.9300 |
P2—C31 | 1.827 (2) | C21—C22 | 1.359 (4) |
P2—C19 | 1.834 (2) | C21—H21 | 0.9300 |
N1—C38 | 1.341 (4) | C22—C23 | 1.366 (4) |
N1—C37 | 1.360 (3) | C22—H22 | 0.9300 |
N1—H1 | 0.856 (10) | C23—C24 | 1.383 (4) |
N2—C40 | 1.317 (4) | C23—H23 | 0.9300 |
N2—C37 | 1.357 (3) | C24—H24 | 0.9300 |
C1—C6 | 1.370 (3) | C25—C30 | 1.386 (3) |
C1—C2 | 1.378 (3) | C25—C26 | 1.391 (3) |
C2—C3 | 1.386 (4) | C26—C27 | 1.384 (4) |
C2—H2 | 0.9300 | C26—H26 | 0.9300 |
C3—C4 | 1.365 (4) | C27—C28 | 1.376 (4) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.363 (4) | C28—C29 | 1.370 (4) |
C4—H4 | 0.9300 | C28—H28 | 0.9300 |
C5—C6 | 1.387 (4) | C29—C30 | 1.382 (4) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—H30 | 0.9300 |
C7—C8 | 1.390 (4) | C31—C32 | 1.390 (3) |
C7—C12 | 1.389 (3) | C31—C36 | 1.395 (3) |
C8—C9 | 1.385 (4) | C32—C33 | 1.382 (3) |
C8—H8 | 0.9300 | C32—H32 | 0.9300 |
C9—C10 | 1.372 (5) | C33—C34 | 1.375 (4) |
C9—H9 | 0.9300 | C33—H33 | 0.9300 |
C10—C11 | 1.367 (5) | C34—C35 | 1.386 (4) |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.385 (4) | C35—C36 | 1.382 (3) |
C11—H11 | 0.9300 | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—H36 | 0.9300 |
C13—C14 | 1.379 (3) | C38—C39 | 1.337 (5) |
C13—C18 | 1.394 (3) | C38—H38 | 0.9300 |
C14—C15 | 1.387 (4) | C39—C40 | 1.380 (5) |
C14—H14 | 0.9300 | C39—H39 | 0.9300 |
C15—C16 | 1.375 (4) | C40—H40 | 0.9300 |
C15—H15 | 0.9300 | ||
P1—Cu1—P2 | 122.45 (2) | C18—C17—H17 | 120.0 |
P1—Cu1—S1 | 102.31 (3) | C16—C17—H17 | 120.0 |
P1—Cu1—Cl1 | 111.76 (2) | C17—C18—C13 | 121.1 (2) |
P2—Cu1—S1 | 112.70 (3) | C17—C18—H18 | 119.4 |
P2—Cu1—Cl1 | 98.77 (2) | C13—C18—H18 | 119.4 |
Cl1—Cu1—S1 | 108.58 (3) | C20—C19—C24 | 117.9 (2) |
C37—S1—Cu1 | 113.20 (9) | C20—C19—P2 | 118.14 (18) |
C13—P1—C7 | 104.70 (11) | C24—C19—P2 | 123.90 (18) |
C13—P1—C1 | 98.99 (10) | C19—C20—C21 | 120.5 (3) |
C7—P1—C1 | 104.61 (11) | C19—C20—H20 | 119.8 |
C13—P1—Cu1 | 119.68 (8) | C21—C20—H20 | 119.8 |
C7—P1—Cu1 | 111.37 (8) | C22—C21—C20 | 121.0 (3) |
C1—P1—Cu1 | 115.69 (8) | C22—C21—H21 | 119.5 |
C25—P2—C31 | 101.63 (10) | C20—C21—H21 | 119.5 |
C25—P2—C19 | 105.01 (10) | C21—C22—C23 | 119.0 (3) |
C31—P2—C19 | 103.09 (10) | C21—C22—H22 | 120.5 |
C25—P2—Cu1 | 117.60 (7) | C23—C22—H22 | 120.5 |
C31—P2—Cu1 | 113.61 (7) | C22—C23—C24 | 120.6 (3) |
C19—P2—Cu1 | 114.15 (8) | C22—C23—H23 | 119.7 |
C38—N1—C37 | 123.1 (3) | C24—C23—H23 | 119.7 |
C38—N1—H1 | 121 (2) | C19—C24—C23 | 120.9 (2) |
C37—N1—H1 | 116 (2) | C19—C24—H24 | 119.5 |
C40—N2—C37 | 118.0 (3) | C23—C24—H24 | 119.5 |
C6—C1—C2 | 118.4 (2) | C30—C25—C26 | 118.5 (2) |
C6—C1—P1 | 117.32 (19) | C30—C25—P2 | 117.29 (18) |
C2—C1—P1 | 123.83 (19) | C26—C25—P2 | 123.99 (18) |
C1—C2—C3 | 120.8 (3) | C27—C26—C25 | 120.4 (3) |
C1—C2—H2 | 119.6 | C27—C26—H26 | 119.8 |
C3—C2—H2 | 119.6 | C25—C26—H26 | 119.8 |
C4—C3—C2 | 119.8 (3) | C28—C27—C26 | 120.1 (3) |
C4—C3—H3 | 120.1 | C28—C27—H27 | 120.0 |
C2—C3—H3 | 120.1 | C26—C27—H27 | 120.0 |
C5—C4—C3 | 120.2 (3) | C29—C28—C27 | 120.1 (3) |
C5—C4—H4 | 119.9 | C29—C28—H28 | 120.0 |
C3—C4—H4 | 119.9 | C27—C28—H28 | 120.0 |
C4—C5—C6 | 119.8 (3) | C28—C29—C30 | 120.2 (3) |
C4—C5—H5 | 120.1 | C28—C29—H29 | 119.9 |
C6—C5—H5 | 120.1 | C30—C29—H29 | 119.9 |
C1—C6—C5 | 121.0 (3) | C29—C30—C25 | 120.7 (3) |
C1—C6—H6 | 119.5 | C29—C30—H30 | 119.7 |
C5—C6—H6 | 119.5 | C25—C30—H30 | 119.7 |
C8—C7—C12 | 118.2 (2) | C32—C31—C36 | 118.4 (2) |
C8—C7—P1 | 119.24 (19) | C32—C31—P2 | 122.16 (17) |
C12—C7—P1 | 122.1 (2) | C36—C31—P2 | 119.24 (17) |
C9—C8—C7 | 120.6 (3) | C33—C32—C31 | 120.9 (2) |
C9—C8—H8 | 119.7 | C33—C32—H32 | 119.6 |
C7—C8—H8 | 119.7 | C31—C32—H32 | 119.6 |
C10—C9—C8 | 120.3 (3) | C34—C33—C32 | 120.3 (2) |
C10—C9—H9 | 119.8 | C34—C33—H33 | 119.8 |
C8—C9—H9 | 119.8 | C32—C33—H33 | 119.8 |
C11—C10—C9 | 119.7 (3) | C33—C34—C35 | 119.7 (2) |
C11—C10—H10 | 120.1 | C33—C34—H34 | 120.2 |
C9—C10—H10 | 120.1 | C35—C34—H34 | 120.2 |
C10—C11—C12 | 120.6 (3) | C36—C35—C34 | 120.3 (2) |
C10—C11—H11 | 119.7 | C36—C35—H35 | 119.9 |
C12—C11—H11 | 119.7 | C34—C35—H35 | 119.9 |
C11—C12—C7 | 120.5 (3) | C35—C36—C31 | 120.5 (2) |
C11—C12—H12 | 119.7 | C35—C36—H36 | 119.8 |
C7—C12—H12 | 119.7 | C31—C36—H36 | 119.8 |
C14—C13—C18 | 118.0 (2) | N1—C37—N2 | 118.0 (2) |
C14—C13—P1 | 119.03 (17) | N1—C37—S1 | 121.25 (19) |
C18—C13—P1 | 122.80 (19) | N2—C37—S1 | 120.8 (2) |
C13—C14—C15 | 121.0 (2) | C39—C38—N1 | 119.6 (3) |
C13—C14—H14 | 119.5 | C39—C38—H38 | 120.2 |
C15—C14—H14 | 119.5 | N1—C38—H38 | 120.2 |
C16—C15—C14 | 120.2 (3) | C38—C39—C40 | 116.4 (3) |
C16—C15—H15 | 119.9 | C38—C39—H39 | 121.8 |
C14—C15—H15 | 119.9 | C40—C39—H39 | 121.8 |
C15—C16—C17 | 119.6 (3) | N2—C40—C39 | 124.8 (3) |
C15—C16—H16 | 120.2 | N2—C40—H40 | 117.6 |
C17—C16—H16 | 120.2 | C39—C40—H40 | 117.6 |
C18—C17—C16 | 120.1 (3) | ||
P1—Cu1—S1—C37 | −120.70 (10) | C14—C15—C16—C17 | 0.9 (4) |
P2—Cu1—S1—C37 | 105.93 (10) | C15—C16—C17—C18 | −0.6 (5) |
Cl1—Cu1—S1—C37 | −2.43 (10) | C16—C17—C18—C13 | −0.5 (5) |
P2—Cu1—P1—C13 | −44.54 (9) | C14—C13—C18—C17 | 1.4 (4) |
Cl1—Cu1—P1—C13 | 72.10 (9) | P1—C13—C18—C17 | 176.7 (2) |
S1—Cu1—P1—C13 | −171.91 (8) | C25—P2—C19—C20 | −93.0 (2) |
P2—Cu1—P1—C7 | 77.92 (9) | C31—P2—C19—C20 | 161.0 (2) |
Cl1—Cu1—P1—C7 | −165.44 (8) | Cu1—P2—C19—C20 | 37.3 (2) |
S1—Cu1—P1—C7 | −49.45 (9) | C25—P2—C19—C24 | 89.6 (2) |
P2—Cu1—P1—C1 | −162.82 (9) | C31—P2—C19—C24 | −16.4 (2) |
Cl1—Cu1—P1—C1 | −46.18 (9) | Cu1—P2—C19—C24 | −140.2 (2) |
S1—Cu1—P1—C1 | 69.81 (9) | C24—C19—C20—C21 | 0.2 (4) |
P1—Cu1—P2—C25 | −65.11 (9) | P2—C19—C20—C21 | −177.4 (2) |
Cl1—Cu1—P2—C25 | 172.02 (8) | C19—C20—C21—C22 | −0.2 (5) |
S1—Cu1—P2—C25 | 57.57 (9) | C20—C21—C22—C23 | 0.2 (5) |
P1—Cu1—P2—C31 | 53.36 (8) | C21—C22—C23—C24 | −0.1 (5) |
Cl1—Cu1—P2—C31 | −69.50 (8) | C20—C19—C24—C23 | −0.1 (4) |
S1—Cu1—P2—C31 | 176.04 (8) | P2—C19—C24—C23 | 177.3 (2) |
P1—Cu1—P2—C19 | 171.20 (8) | C22—C23—C24—C19 | 0.0 (5) |
Cl1—Cu1—P2—C19 | 48.33 (8) | C31—P2—C25—C30 | −101.28 (19) |
S1—Cu1—P2—C19 | −66.12 (8) | C19—P2—C25—C30 | 151.59 (18) |
C13—P1—C1—C6 | −86.4 (2) | Cu1—P2—C25—C30 | 23.4 (2) |
C7—P1—C1—C6 | 165.7 (2) | C31—P2—C25—C26 | 73.4 (2) |
Cu1—P1—C1—C6 | 42.8 (2) | C19—P2—C25—C26 | −33.7 (2) |
C13—P1—C1—C2 | 85.5 (2) | Cu1—P2—C25—C26 | −161.88 (18) |
C7—P1—C1—C2 | −22.4 (3) | C30—C25—C26—C27 | 0.2 (4) |
Cu1—P1—C1—C2 | −145.3 (2) | P2—C25—C26—C27 | −174.5 (2) |
C6—C1—C2—C3 | 1.5 (5) | C25—C26—C27—C28 | 1.2 (4) |
P1—C1—C2—C3 | −170.3 (3) | C26—C27—C28—C29 | −1.2 (5) |
C1—C2—C3—C4 | −1.1 (5) | C27—C28—C29—C30 | −0.2 (5) |
C2—C3—C4—C5 | 0.3 (6) | C28—C29—C30—C25 | 1.6 (4) |
C3—C4—C5—C6 | 0.0 (6) | C26—C25—C30—C29 | −1.6 (4) |
C2—C1—C6—C5 | −1.2 (5) | P2—C25—C30—C29 | 173.4 (2) |
P1—C1—C6—C5 | 171.2 (3) | C25—P2—C31—C32 | 19.2 (2) |
C4—C5—C6—C1 | 0.5 (5) | C19—P2—C31—C32 | 127.86 (18) |
C13—P1—C7—C8 | −163.41 (19) | Cu1—P2—C31—C32 | −108.07 (17) |
C1—P1—C7—C8 | −59.8 (2) | C25—P2—C31—C36 | −165.89 (17) |
Cu1—P1—C7—C8 | 65.9 (2) | C19—P2—C31—C36 | −57.27 (19) |
C13—P1—C7—C12 | 25.0 (2) | Cu1—P2—C31—C36 | 66.79 (18) |
C1—P1—C7—C12 | 128.6 (2) | C36—C31—C32—C33 | −0.3 (3) |
Cu1—P1—C7—C12 | −105.7 (2) | P2—C31—C32—C33 | 174.58 (18) |
C12—C7—C8—C9 | −1.4 (4) | C31—C32—C33—C34 | 0.9 (4) |
P1—C7—C8—C9 | −173.3 (2) | C32—C33—C34—C35 | −0.5 (4) |
C7—C8—C9—C10 | 1.3 (4) | C33—C34—C35—C36 | −0.6 (4) |
C8—C9—C10—C11 | −0.4 (5) | C34—C35—C36—C31 | 1.1 (4) |
C9—C10—C11—C12 | −0.3 (5) | C32—C31—C36—C35 | −0.7 (3) |
C10—C11—C12—C7 | 0.1 (5) | P2—C31—C36—C35 | −175.74 (18) |
C8—C7—C12—C11 | 0.7 (4) | C38—N1—C37—N2 | 1.6 (4) |
P1—C7—C12—C11 | 172.3 (2) | C38—N1—C37—S1 | −178.0 (3) |
C7—P1—C13—C14 | −132.36 (19) | C40—N2—C37—N1 | −0.4 (4) |
C1—P1—C13—C14 | 119.85 (19) | C40—N2—C37—S1 | 179.2 (2) |
Cu1—P1—C13—C14 | −6.7 (2) | Cu1—S1—C37—N1 | −4.8 (3) |
C7—P1—C13—C18 | 52.3 (2) | Cu1—S1—C37—N2 | 175.6 (2) |
C1—P1—C13—C18 | −55.4 (2) | C37—N1—C38—C39 | −0.7 (5) |
Cu1—P1—C13—C18 | 178.02 (18) | N1—C38—C39—C40 | −1.2 (6) |
C18—C13—C14—C15 | −1.1 (4) | C37—N2—C40—C39 | −1.8 (5) |
P1—C13—C14—C15 | −176.6 (2) | C38—C39—C40—N2 | 2.6 (6) |
C13—C14—C15—C16 | 0.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.86 (1) | 2.20 (1) | 3.049 (2) | 175 (3) |
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