In the title compound, [Cu(C12H13O2)2(C6H6N2O)], a nicotinamide adduct of bis(3-benzylpentane-2,4-dionato)copper(II), the metal ion exhibits a square-pyramidal coordination environment. The molecules of the complex self-assemble in the solid state by way of amide-to-amide hydrogen bonds to form one-dimensional polymers.
Supporting information
CCDC reference: 298393
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.052
- wR factor = 0.151
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.180
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.18
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.36 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O22 - C24 .. 6.62 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C211
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT353_ALERT_3_C Long N-H Bond (0.87A) N32 - H1N ... 1.06 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H210 .. O31 .. 2.67 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997),
Mercury (Version 1.2.1; Bruno et al., 2002),
RasTop (Valadon, 2004) and
POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).
bis(3-benzylpentane-2,4-dionato)(nicotinamide)copper(II)
top
Crystal data top
[Cu(C12H13O2)2(C6H6N2O)] | F(000) = 1180 |
Mr = 564.13 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 34 reflections |
a = 12.3775 (18) Å | θ = 10.1–16.4° |
b = 22.5695 (19) Å | µ = 0.82 mm−1 |
c = 10.0534 (12) Å | T = 298 K |
β = 93.018 (8)° | Plate, green |
V = 2804.6 (6) Å3 | 0.58 × 0.37 × 0.07 mm |
Z = 4 | |
Data collection top
Philips PW1100 diffractometer | 2868 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.180 |
Graphite monochromator | θmax = 27.0°, θmin = 2.2° |
ω scans | h = 0→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −28→0 |
Tmin = 0.688, Tmax = 0.946 | l = −12→12 |
6404 measured reflections | 3 standard reflections every 120 min |
6128 independent reflections | intensity decay: 3.8% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0738P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.151 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.27 e Å−3 |
6128 reflections | Δρmin = −0.55 e Å−3 |
343 parameters | |
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. All non-hydrogen atoms were included in the refinement according
to the anisotropic model. Coordinates of hydrogen atoms bonded to carbon atoms
were calculated following the stereochemical rules with C—H distances of
0.93 for phenyl, 0.97 Å for methylene and 0.96 Å for methyl groups. The
hydrogen atoms were included in the refinement using the riding-model
approximation. Uiso(H) were defined as 1.2Ueq of the parent
carbon atoms for phenyl and methylene residues and 1.5Ueq of the
parent carbon atoms for the methyl groups. The hydrogen atoms of the amide
group have been located from the final Fourier difference map, their
coordinates were blocked during the refinement process and the isotropic
thermal parameter was set at 1.5 times the average thermal parameter of the
belonging nitrogen atom. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu | 0.03227 (4) | 0.06902 (2) | 0.19038 (5) | 0.03985 (17) | |
O11 | −0.0047 (2) | −0.01282 (11) | 0.2116 (3) | 0.0447 (7) | |
O12 | −0.0857 (2) | 0.08018 (11) | 0.0595 (3) | 0.0438 (7) | |
O21 | 0.1622 (2) | 0.05555 (12) | 0.3022 (3) | 0.0506 (7) | |
O22 | 0.0850 (2) | 0.14623 (11) | 0.1426 (3) | 0.0437 (7) | |
O31 | −0.1143 (3) | 0.25055 (13) | 0.6878 (3) | 0.0563 (8) | |
N31 | −0.0629 (3) | 0.10008 (15) | 0.3732 (3) | 0.0472 (9) | |
N32 | −0.0985 (3) | 0.28264 (13) | 0.4780 (3) | 0.0466 (9) | |
C11 | −0.0943 (4) | −0.10362 (17) | 0.2070 (5) | 0.0587 (12) | |
H11A | −0.0301 | −0.1138 | 0.2598 | 0.088* | |
H11B | −0.1006 | −0.1288 | 0.13 | 0.088* | |
H11C | −0.1565 | −0.1089 | 0.259 | 0.088* | |
C12 | −0.0877 (3) | −0.03950 (17) | 0.1631 (4) | 0.0420 (10) | |
C13 | −0.1676 (3) | −0.01525 (17) | 0.0759 (4) | 0.0421 (10) | |
C14 | −0.1609 (3) | 0.04327 (18) | 0.0278 (4) | 0.0403 (9) | |
C15 | −0.2444 (4) | 0.06743 (19) | −0.0741 (5) | 0.0615 (12) | |
H15A | −0.2248 | 0.107 | −0.0984 | 0.092* | |
H15B | −0.3142 | 0.0679 | −0.0367 | 0.092* | |
H15C | −0.247 | 0.0427 | −0.1519 | 0.092* | |
C16 | −0.2632 (3) | −0.05423 (18) | 0.0304 (4) | 0.0489 (11) | |
H16A | −0.2948 | −0.0383 | −0.0524 | 0.059* | |
H16B | −0.2362 | −0.0935 | 0.0118 | 0.059* | |
C17 | −0.3519 (3) | −0.0600 (2) | 0.1281 (4) | 0.0512 (11) | |
C18 | −0.4003 (4) | −0.1139 (2) | 0.1522 (5) | 0.0697 (15) | |
H18 | −0.3766 | −0.1477 | 0.1096 | 0.084* | |
C19 | −0.4836 (5) | −0.1185 (3) | 0.2384 (6) | 0.094 (2) | |
H19 | −0.5154 | −0.1552 | 0.2522 | 0.112* | |
C110 | −0.5189 (4) | −0.0703 (4) | 0.3028 (6) | 0.096 (2) | |
H110 | −0.5747 | −0.0738 | 0.3606 | 0.115* | |
C111 | −0.4724 (5) | −0.0163 (3) | 0.2827 (6) | 0.0896 (19) | |
H111 | −0.4962 | 0.017 | 0.327 | 0.108* | |
C112 | −0.3896 (4) | −0.0117 (2) | 0.1959 (5) | 0.0679 (14) | |
H112 | −0.3583 | 0.0251 | 0.1829 | 0.081* | |
C21 | 0.3043 (4) | 0.0732 (2) | 0.4596 (5) | 0.0694 (14) | |
H21A | 0.2765 | 0.0816 | 0.5449 | 0.104* | |
H21B | 0.3725 | 0.093 | 0.4525 | 0.104* | |
H21C | 0.3143 | 0.0313 | 0.4505 | 0.104* | |
C22 | 0.2254 (3) | 0.09497 (19) | 0.3510 (4) | 0.0463 (10) | |
C23 | 0.2292 (3) | 0.15466 (18) | 0.3095 (4) | 0.0454 (10) | |
C24 | 0.1604 (3) | 0.17523 (17) | 0.2038 (4) | 0.0459 (10) | |
C25 | 0.1720 (4) | 0.23775 (19) | 0.1506 (6) | 0.0726 (15) | |
H25A | 0.135 | 0.2407 | 0.0645 | 0.109* | |
H25B | 0.2473 | 0.2467 | 0.143 | 0.109* | |
H25C | 0.1412 | 0.2653 | 0.2106 | 0.109* | |
C26 | 0.3123 (4) | 0.1958 (2) | 0.3765 (5) | 0.0610 (13) | |
H26A | 0.2867 | 0.2362 | 0.3646 | 0.073* | |
H26B | 0.3154 | 0.1876 | 0.4714 | 0.073* | |
C27 | 0.4257 (4) | 0.19249 (19) | 0.3294 (5) | 0.0557 (12) | |
C28 | 0.4513 (4) | 0.1632 (2) | 0.2142 (6) | 0.0713 (15) | |
H28 | 0.3968 | 0.144 | 0.1636 | 0.086* | |
C29 | 0.5565 (4) | 0.1619 (3) | 0.1724 (7) | 0.095 (2) | |
H29 | 0.5711 | 0.1433 | 0.0928 | 0.113* | |
C210 | 0.6376 (5) | 0.1876 (3) | 0.2467 (9) | 0.114 (3) | |
H210 | 0.7087 | 0.1844 | 0.222 | 0.136* | |
C211 | 0.6138 (5) | 0.2181 (3) | 0.3581 (10) | 0.122 (3) | |
H211 | 0.6684 | 0.2385 | 0.4058 | 0.146* | |
C212 | 0.5086 (5) | 0.2193 (2) | 0.4020 (7) | 0.093 (2) | |
H212 | 0.4947 | 0.2384 | 0.4813 | 0.112* | |
C31 | −0.0650 (3) | 0.15736 (16) | 0.4110 (4) | 0.0388 (9) | |
H31 | −0.0299 | 0.185 | 0.36 | 0.047* | |
C32 | −0.1158 (3) | 0.17711 (16) | 0.5205 (4) | 0.0364 (9) | |
C33 | −0.1688 (4) | 0.13585 (19) | 0.5957 (4) | 0.0561 (12) | |
H33 | −0.2048 | 0.1477 | 0.6701 | 0.067* | |
C34 | −0.1673 (4) | 0.07737 (18) | 0.5588 (5) | 0.0667 (14) | |
H34 | −0.2021 | 0.0488 | 0.6078 | 0.08* | |
C35 | −0.1138 (4) | 0.06183 (18) | 0.4488 (4) | 0.0543 (11) | |
H35 | −0.1128 | 0.022 | 0.4252 | 0.065* | |
C36 | −0.1099 (3) | 0.24020 (17) | 0.5687 (4) | 0.0386 (9) | |
H1N | −0.1036 | 0.272 | 0.3749 | 0.069* | |
H2N | −0.0642 | 0.3224 | 0.4935 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0375 (3) | 0.0319 (2) | 0.0503 (3) | −0.0019 (2) | 0.0032 (2) | 0.0003 (2) |
O11 | 0.0453 (17) | 0.0330 (14) | 0.0551 (18) | −0.0025 (13) | −0.0033 (14) | −0.0019 (13) |
O12 | 0.0445 (16) | 0.0392 (16) | 0.0478 (16) | −0.0011 (12) | 0.0013 (13) | 0.0011 (12) |
O21 | 0.0404 (16) | 0.0425 (17) | 0.068 (2) | −0.0038 (13) | −0.0087 (14) | 0.0072 (14) |
O22 | 0.0365 (15) | 0.0361 (14) | 0.0585 (18) | −0.0063 (13) | 0.0024 (13) | 0.0042 (13) |
O31 | 0.081 (2) | 0.0550 (19) | 0.0341 (17) | −0.0036 (16) | 0.0127 (15) | −0.0067 (14) |
N31 | 0.057 (2) | 0.0389 (19) | 0.047 (2) | 0.0037 (17) | 0.0134 (17) | 0.0010 (17) |
N32 | 0.065 (2) | 0.0344 (18) | 0.040 (2) | −0.0083 (17) | 0.0023 (17) | 0.0012 (15) |
C11 | 0.056 (3) | 0.034 (2) | 0.085 (3) | −0.005 (2) | 0.003 (2) | 0.005 (2) |
C12 | 0.043 (3) | 0.037 (2) | 0.047 (2) | −0.0002 (19) | 0.009 (2) | −0.0092 (19) |
C13 | 0.041 (2) | 0.042 (2) | 0.043 (2) | −0.0025 (19) | 0.0091 (19) | −0.0065 (19) |
C14 | 0.038 (2) | 0.046 (2) | 0.038 (2) | −0.0022 (19) | 0.0035 (18) | −0.0047 (18) |
C15 | 0.061 (3) | 0.059 (3) | 0.063 (3) | −0.007 (2) | −0.012 (2) | 0.005 (2) |
C16 | 0.051 (3) | 0.048 (2) | 0.048 (3) | −0.012 (2) | 0.005 (2) | −0.008 (2) |
C17 | 0.037 (2) | 0.062 (3) | 0.054 (3) | −0.004 (2) | −0.0043 (19) | −0.001 (2) |
C18 | 0.061 (3) | 0.077 (4) | 0.071 (4) | −0.025 (3) | 0.002 (3) | 0.002 (3) |
C19 | 0.075 (4) | 0.128 (6) | 0.077 (4) | −0.049 (4) | −0.001 (3) | 0.016 (4) |
C110 | 0.043 (3) | 0.175 (8) | 0.071 (4) | −0.010 (4) | 0.008 (3) | 0.019 (5) |
C111 | 0.062 (4) | 0.126 (5) | 0.082 (4) | 0.028 (4) | 0.024 (3) | 0.002 (4) |
C112 | 0.058 (3) | 0.070 (3) | 0.077 (4) | 0.009 (3) | 0.016 (3) | 0.007 (3) |
C21 | 0.060 (3) | 0.072 (3) | 0.074 (3) | −0.007 (3) | −0.011 (3) | 0.008 (3) |
C22 | 0.037 (2) | 0.050 (2) | 0.053 (3) | 0.001 (2) | 0.010 (2) | −0.004 (2) |
C23 | 0.032 (2) | 0.045 (2) | 0.060 (3) | −0.0053 (19) | 0.013 (2) | −0.010 (2) |
C24 | 0.039 (2) | 0.038 (2) | 0.064 (3) | −0.0005 (19) | 0.025 (2) | −0.002 (2) |
C25 | 0.062 (3) | 0.050 (3) | 0.105 (4) | −0.016 (2) | 0.003 (3) | 0.015 (3) |
C26 | 0.063 (3) | 0.052 (3) | 0.068 (3) | −0.011 (2) | 0.006 (3) | −0.017 (2) |
C27 | 0.043 (3) | 0.042 (2) | 0.081 (3) | −0.009 (2) | −0.004 (2) | 0.002 (2) |
C28 | 0.036 (3) | 0.083 (4) | 0.095 (4) | −0.011 (3) | 0.007 (3) | −0.005 (3) |
C29 | 0.043 (3) | 0.124 (6) | 0.118 (5) | 0.010 (3) | 0.017 (3) | 0.024 (4) |
C210 | 0.037 (4) | 0.124 (7) | 0.181 (8) | −0.002 (4) | 0.016 (5) | 0.054 (6) |
C211 | 0.041 (4) | 0.118 (6) | 0.202 (9) | −0.024 (4) | −0.034 (5) | 0.011 (6) |
C212 | 0.065 (4) | 0.080 (4) | 0.131 (5) | −0.010 (3) | −0.031 (4) | −0.009 (4) |
C31 | 0.042 (2) | 0.037 (2) | 0.038 (2) | 0.0016 (18) | 0.0068 (18) | 0.0064 (17) |
C32 | 0.041 (2) | 0.036 (2) | 0.032 (2) | 0.0013 (17) | 0.0026 (17) | 0.0020 (17) |
C33 | 0.075 (3) | 0.052 (3) | 0.044 (3) | −0.008 (2) | 0.027 (2) | −0.001 (2) |
C34 | 0.097 (4) | 0.043 (3) | 0.063 (3) | −0.017 (3) | 0.034 (3) | 0.003 (2) |
C35 | 0.073 (3) | 0.034 (2) | 0.057 (3) | 0.003 (2) | 0.016 (2) | 0.002 (2) |
C36 | 0.034 (2) | 0.044 (2) | 0.039 (2) | 0.0013 (18) | 0.0041 (17) | −0.0042 (19) |
Geometric parameters (Å, º) top
Cu—O11 | 1.918 (3) | C111—C112 | 1.385 (7) |
Cu—O12 | 1.930 (3) | C111—H111 | 0.93 |
Cu—O22 | 1.930 (2) | C112—H112 | 0.93 |
Cu—O21 | 1.937 (3) | C21—C22 | 1.508 (6) |
Cu—N31 | 2.342 (3) | C21—H21A | 0.96 |
O11—C12 | 1.266 (4) | C21—H21B | 0.96 |
O12—C14 | 1.277 (4) | C21—H21C | 0.96 |
O21—C22 | 1.266 (5) | C22—C23 | 1.412 (6) |
O22—C24 | 1.272 (5) | C23—C24 | 1.405 (6) |
O31—C36 | 1.224 (4) | C23—C26 | 1.517 (5) |
N31—C35 | 1.331 (5) | C24—C25 | 1.518 (5) |
N31—C31 | 1.348 (5) | C25—H25A | 0.96 |
N32—C36 | 1.335 (5) | C25—H25B | 0.96 |
N32—H1N | 1.06 | C25—H25C | 0.96 |
N32—H2N | 1.00 | C26—C27 | 1.507 (6) |
C11—C12 | 1.516 (5) | C26—H26A | 0.97 |
C11—H11A | 0.96 | C26—H26B | 0.97 |
C11—H11B | 0.96 | C27—C212 | 1.368 (6) |
C11—H11C | 0.96 | C27—C28 | 1.384 (7) |
C12—C13 | 1.398 (5) | C28—C29 | 1.390 (7) |
C13—C14 | 1.410 (5) | C28—H28 | 0.93 |
C13—C16 | 1.526 (5) | C29—C210 | 1.349 (9) |
C14—C15 | 1.518 (6) | C29—H29 | 0.93 |
C15—H15A | 0.96 | C210—C211 | 1.360 (10) |
C15—H15B | 0.96 | C210—H210 | 0.93 |
C15—H15C | 0.96 | C211—C212 | 1.397 (9) |
C16—C17 | 1.516 (6) | C211—H211 | 0.93 |
C16—H16A | 0.97 | C212—H212 | 0.93 |
C16—H16B | 0.97 | C31—C32 | 1.370 (5) |
C17—C112 | 1.381 (6) | C31—H31 | 0.93 |
C17—C18 | 1.383 (6) | C32—C33 | 1.387 (5) |
C18—C19 | 1.385 (8) | C32—C36 | 1.505 (5) |
C18—H18 | 0.93 | C33—C34 | 1.371 (6) |
C19—C110 | 1.350 (8) | C33—H33 | 0.93 |
C19—H19 | 0.93 | C34—C35 | 1.365 (6) |
C110—C111 | 1.367 (8) | C34—H34 | 0.93 |
C110—H110 | 0.93 | C35—H35 | 0.93 |
| | | |
O11—Cu—O12 | 91.43 (11) | C111—C112—H112 | 118.9 |
O11—Cu—O22 | 169.43 (12) | C22—C21—H21A | 109.5 |
O12—Cu—O22 | 88.06 (11) | C22—C21—H21B | 109.5 |
O11—Cu—O21 | 88.86 (11) | H21A—C21—H21B | 109.5 |
O12—Cu—O21 | 172.49 (12) | C22—C21—H21C | 109.5 |
O22—Cu—O21 | 90.28 (11) | H21A—C21—H21C | 109.5 |
O11—Cu—N31 | 93.92 (12) | H21B—C21—H21C | 109.5 |
O12—Cu—N31 | 95.86 (12) | O21—C22—C23 | 125.8 (4) |
O22—Cu—N31 | 96.64 (12) | O21—C22—C21 | 114.5 (4) |
O21—Cu—N31 | 91.61 (12) | C23—C22—C21 | 119.6 (4) |
C12—O11—Cu | 127.5 (3) | C24—C23—C22 | 120.7 (4) |
C14—O12—Cu | 126.9 (3) | C24—C23—C26 | 120.2 (4) |
C22—O21—Cu | 126.3 (3) | C22—C23—C26 | 119.0 (4) |
C24—O22—Cu | 126.4 (3) | O22—C24—C23 | 126.6 (4) |
C35—N31—C31 | 116.4 (3) | O22—C24—C25 | 112.9 (4) |
C35—N31—Cu | 121.8 (3) | C23—C24—C25 | 120.6 (4) |
C31—N31—Cu | 121.8 (3) | C24—C25—H25A | 109.5 |
C36—N32—H1N | 120 | C24—C25—H25B | 109.5 |
C36—N32—H2N | 127 | H25A—C25—H25B | 109.5 |
H1N—N32—H2N | 111 | C24—C25—H25C | 109.5 |
C12—C11—H11A | 109.5 | H25A—C25—H25C | 109.5 |
C12—C11—H11B | 109.5 | H25B—C25—H25C | 109.5 |
H11A—C11—H11B | 109.5 | C27—C26—C23 | 116.8 (4) |
C12—C11—H11C | 109.5 | C27—C26—H26A | 108.1 |
H11A—C11—H11C | 109.5 | C23—C26—H26A | 108.1 |
H11B—C11—H11C | 109.5 | C27—C26—H26B | 108.1 |
O11—C12—C13 | 126.0 (4) | C23—C26—H26B | 108.1 |
O11—C12—C11 | 113.4 (4) | H26A—C26—H26B | 107.3 |
C13—C12—C11 | 120.6 (4) | C212—C27—C28 | 117.3 (5) |
C12—C13—C14 | 122.0 (4) | C212—C27—C26 | 119.6 (5) |
C12—C13—C16 | 118.3 (4) | C28—C27—C26 | 123.0 (4) |
C14—C13—C16 | 119.7 (4) | C27—C28—C29 | 121.5 (5) |
O12—C14—C13 | 125.5 (4) | C27—C28—H28 | 119.3 |
O12—C14—C15 | 113.3 (4) | C29—C28—H28 | 119.3 |
C13—C14—C15 | 121.2 (4) | C210—C29—C28 | 120.4 (7) |
C14—C15—H15A | 109.5 | C210—C29—H29 | 119.8 |
C14—C15—H15B | 109.5 | C28—C29—H29 | 119.8 |
H15A—C15—H15B | 109.5 | C29—C210—C211 | 119.1 (6) |
C14—C15—H15C | 109.5 | C29—C210—H210 | 120.5 |
H15A—C15—H15C | 109.5 | C211—C210—H210 | 120.5 |
H15B—C15—H15C | 109.5 | C210—C211—C212 | 121.0 (6) |
C17—C16—C13 | 115.6 (3) | C210—C211—H211 | 119.5 |
C17—C16—H16A | 108.4 | C212—C211—H211 | 119.5 |
C13—C16—H16A | 108.4 | C27—C212—C211 | 120.5 (7) |
C17—C16—H16B | 108.4 | C27—C212—H212 | 119.7 |
C13—C16—H16B | 108.4 | C211—C212—H212 | 119.7 |
H16A—C16—H16B | 107.4 | N31—C31—C32 | 123.7 (4) |
C112—C17—C18 | 116.5 (4) | N31—C31—H31 | 118.1 |
C112—C17—C16 | 121.8 (4) | C32—C31—H31 | 118.1 |
C18—C17—C16 | 121.7 (4) | C31—C32—C33 | 118.0 (4) |
C17—C18—C19 | 121.3 (5) | C31—C32—C36 | 123.4 (3) |
C17—C18—H18 | 119.3 | C33—C32—C36 | 118.4 (4) |
C19—C18—H18 | 119.3 | C34—C33—C32 | 119.0 (4) |
C110—C19—C18 | 120.6 (6) | C34—C33—H33 | 120.5 |
C110—C19—H19 | 119.7 | C32—C33—H33 | 120.5 |
C18—C19—H19 | 119.7 | C35—C34—C33 | 118.7 (4) |
C19—C110—C111 | 120.0 (5) | C35—C34—H34 | 120.6 |
C19—C110—H110 | 120 | C33—C34—H34 | 120.6 |
C111—C110—H110 | 120 | N31—C35—C34 | 124.1 (4) |
C110—C111—C112 | 119.4 (6) | N31—C35—H35 | 117.9 |
C110—C111—H111 | 120.3 | C34—C35—H35 | 117.9 |
C112—C111—H111 | 120.3 | O31—C36—N32 | 122.9 (4) |
C17—C112—C111 | 122.2 (5) | O31—C36—C32 | 119.4 (4) |
C17—C112—H112 | 118.9 | N32—C36—C32 | 117.7 (3) |
| | | |
O12—Cu—O11—C12 | −8.0 (3) | C19—C110—C111—C112 | 0.2 (9) |
O22—Cu—O11—C12 | −95.1 (7) | C18—C17—C112—C111 | −0.7 (7) |
O21—Cu—O11—C12 | 179.5 (3) | C16—C17—C112—C111 | 178.3 (5) |
N31—Cu—O11—C12 | 87.9 (3) | C110—C111—C112—C17 | 0.1 (8) |
O11—Cu—O12—C14 | 8.4 (3) | Cu—O21—C22—C23 | −16.1 (6) |
O22—Cu—O12—C14 | 177.9 (3) | Cu—O21—C22—C21 | 166.1 (3) |
N31—Cu—O12—C14 | −85.7 (3) | O21—C22—C23—C24 | −1.1 (6) |
O11—Cu—O21—C22 | −169.1 (3) | C21—C22—C23—C24 | 176.6 (4) |
O22—Cu—O21—C22 | 21.4 (3) | O21—C22—C23—C26 | −178.3 (4) |
N31—Cu—O21—C22 | −75.2 (3) | C21—C22—C23—C26 | −0.6 (6) |
O11—Cu—O22—C24 | −102.6 (7) | Cu—O22—C24—C23 | 7.7 (6) |
O12—Cu—O22—C24 | 170.0 (3) | Cu—O22—C24—C25 | −172.6 (3) |
O21—Cu—O22—C24 | −17.3 (3) | C22—C23—C24—O22 | 5.6 (6) |
N31—Cu—O22—C24 | 74.3 (3) | C26—C23—C24—O22 | −177.2 (4) |
O11—Cu—N31—C35 | 2.0 (3) | C22—C23—C24—C25 | −174.0 (4) |
O12—Cu—N31—C35 | 93.8 (3) | C26—C23—C24—C25 | 3.1 (6) |
O22—Cu—N31—C35 | −177.5 (3) | C24—C23—C26—C27 | −96.6 (5) |
O21—Cu—N31—C35 | −87.0 (3) | C22—C23—C26—C27 | 80.6 (5) |
O11—Cu—N31—C31 | 178.9 (3) | C23—C26—C27—C212 | −167.1 (5) |
O12—Cu—N31—C31 | −89.2 (3) | C23—C26—C27—C28 | 12.8 (7) |
O22—Cu—N31—C31 | −0.5 (3) | C212—C27—C28—C29 | −1.2 (8) |
O21—Cu—N31—C31 | 90.0 (3) | C26—C27—C28—C29 | 178.9 (5) |
Cu—O11—C12—C13 | 4.3 (6) | C27—C28—C29—C210 | 2.6 (9) |
Cu—O11—C12—C11 | −176.6 (3) | C28—C29—C210—C211 | −4.4 (11) |
O11—C12—C13—C14 | 2.4 (6) | C29—C210—C211—C212 | 5.0 (12) |
C11—C12—C13—C14 | −176.7 (4) | C28—C27—C212—C211 | 1.8 (8) |
O11—C12—C13—C16 | −178.7 (4) | C26—C27—C212—C211 | −178.3 (5) |
C11—C12—C13—C16 | 2.2 (5) | C210—C211—C212—C27 | −3.8 (11) |
Cu—O12—C14—C13 | −5.2 (6) | C35—N31—C31—C32 | −0.1 (6) |
Cu—O12—C14—C15 | 177.1 (3) | Cu—N31—C31—C32 | −177.2 (3) |
C12—C13—C14—O12 | −1.9 (6) | N31—C31—C32—C33 | −0.6 (6) |
C16—C13—C14—O12 | 179.3 (3) | N31—C31—C32—C36 | 174.7 (3) |
C12—C13—C14—C15 | 175.7 (4) | C31—C32—C33—C34 | 0.7 (6) |
C16—C13—C14—C15 | −3.2 (6) | C36—C32—C33—C34 | −174.8 (4) |
C12—C13—C16—C17 | 80.4 (5) | C32—C33—C34—C35 | −0.2 (7) |
C14—C13—C16—C17 | −100.7 (5) | C31—N31—C35—C34 | 0.6 (7) |
C13—C16—C17—C112 | 43.7 (6) | Cu—N31—C35—C34 | 177.8 (4) |
C13—C16—C17—C18 | −137.3 (4) | C33—C34—C35—N31 | −0.5 (8) |
C112—C17—C18—C19 | 1.0 (7) | C31—C32—C36—O31 | −149.0 (4) |
C16—C17—C18—C19 | −178.0 (5) | C33—C32—C36—O31 | 26.2 (6) |
C17—C18—C19—C110 | −0.8 (9) | C31—C32—C36—N32 | 30.2 (5) |
C18—C19—C110—C111 | 0.1 (9) | C33—C32—C36—N32 | −154.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N32—H1N···O31i | 1.06 | 1.95 | 3.008 (4) | 178 |
N32—H2N···O22ii | 1.00 | 2.42 | 3.174 (4) | 131 |
N32—H2N···O12ii | 1.00 | 2.32 | 3.205 (4) | 147 |
C31—H31···O31i | 0.93 | 2.45 | 3.096 (5) | 126 |
C210—H210···O31iii | 0.93 | 2.67 | 3.453 (7) | 142 |
C34—H34···O21iv | 0.93 | 2.56 | 3.309 (5) | 138 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z−1/2; (iv) −x, −y, −z+1. |