In the title compound, [CuCl(C12H8N2)2](C8H4NO6)·2H2O, the coordination geometry of the Cu atom is best described as distorted trigonal bipyramidal, made up of four N atoms of two phenanthroline molecules and one chloride anion. The 5-nitroisophthalate(1−) anion is uncomplexed and balances the charge. π–π stacking and intermolecular hydrogen-bond interactions link the components units into a three-dimensional network structure.
Supporting information
CCDC reference: 252948
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.013 Å
- R factor = 0.103
- wR factor = 0.204
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.103
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.59
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O3
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13
PLAT417_ALERT_2_C Short Inter D-H..H-D H2A .. H7A .. 2.15 Ang.
PLAT731_ALERT_1_C Bond Calc 0.80(5), Rep 0.805(19) ...... 2.63 su-Rat
O7 -H7A 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.83(7), Rep 0.83(2) ...... 3.50 su-Rat
O8 -H8A 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.82(6), Rep 0.82(2) ...... 3.00 su-Rat
O8 -H8B 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.
Chlorobis(1,10-phenanthroline)copper(II) 5-nitroisophthalate(1-) dihydrate
top
Crystal data top
[CuCl(C12H8N2)2](C8H4NO6)·2H2O | Z = 2 |
Mr = 705.55 | F(000) = 722 |
Triclinic, P1 | Dx = 1.566 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5099 (13) Å | Cell parameters from 476 reflections |
b = 12.1597 (14) Å | θ = 2.6–24.1° |
c = 12.5348 (14) Å | µ = 0.88 mm−1 |
α = 72.798 (3)° | T = 298 K |
β = 84.990 (2)° | Rod, blue |
γ = 77.968 (3)° | 0.13 × 0.06 × 0.05 mm |
V = 1496.1 (3) Å3 | |
Data collection top
Bruker APEX area-detector diffractometer | 5344 independent reflections |
Radiation source: fine-focus sealed tube | 3112 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
φ and ω scans | θmax = 25.2°, θmin = 1.7° |
Absorption correction: integration (SADABS; Bruker, 2002) | h = −12→12 |
Tmin = 0.894, Tmax = 0.957 | k = −14→14 |
11046 measured reflections | l = −15→15 |
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)] = 0.103 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.4686P] where P = (Fo2 + 2Fc2)/3 |
5344 reflections | (Δ/σ)max = 0.003 |
437 parameters | Δρmax = 0.49 e Å−3 |
6 restraints | Δρmin = −0.44 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 | |
Cu1 | 0.26184 (9) | 0.49728 (8) | 0.30213 (8) | 0.0302 (3) | |
Cl1 | 0.4402 (2) | 0.36824 (19) | 0.3863 (2) | 0.0509 (7) | |
O1 | 0.2263 (7) | 0.9229 (7) | 0.6847 (6) | 0.085 (3) | |
O2 | 0.3405 (6) | 1.0228 (5) | 0.7469 (5) | 0.0510 (17) | |
H2A | 0.4130 | 0.9814 | 0.7589 | 0.077* | |
O3 | 0.3015 (6) | 1.0220 (5) | 1.1377 (5) | 0.0518 (18) | |
O4 | 0.1602 (6) | 0.9320 (5) | 1.2542 (5) | 0.0483 (17) | |
O5 | −0.0752 (8) | 0.7122 (7) | 0.9404 (7) | 0.095 (3) | |
O6 | −0.1052 (8) | 0.7212 (7) | 1.1073 (6) | 0.092 (3) | |
O7 | 0.4099 (7) | 0.0468 (5) | 0.2990 (5) | 0.0522 (17) | |
O8 | 0.3724 (10) | 0.9029 (11) | 0.5063 (6) | 0.143 (4) | |
N1 | 0.1512 (6) | 0.3758 (6) | 0.3277 (5) | 0.0336 (17) | |
N2 | 0.0868 (6) | 0.5927 (5) | 0.3455 (5) | 0.0306 (16) | |
N3 | 0.2745 (6) | 0.5367 (6) | 0.1216 (6) | 0.0360 (17) | |
N4 | 0.3627 (6) | 0.6272 (5) | 0.2637 (5) | 0.0316 (16) | |
N5 | −0.0519 (8) | 0.7450 (7) | 1.0166 (7) | 0.053 (2) | |
C1 | 0.1872 (9) | 0.2648 (8) | 0.3258 (7) | 0.046 (2) | |
H1 | 0.2749 | 0.2366 | 0.3138 | 0.055* | |
C2 | 0.1019 (9) | 0.1895 (9) | 0.3405 (8) | 0.055 (3) | |
H2 | 0.1319 | 0.1118 | 0.3407 | 0.066* | |
C3 | −0.0292 (9) | 0.2312 (9) | 0.3550 (7) | 0.048 (3) | |
H3A | −0.0893 | 0.1831 | 0.3618 | 0.057* | |
C4 | −0.0705 (8) | 0.3475 (8) | 0.3594 (6) | 0.034 (2) | |
C5 | −0.2036 (9) | 0.3972 (9) | 0.3767 (7) | 0.047 (2) | |
H5 | −0.2675 | 0.3533 | 0.3814 | 0.056* | |
C6 | −0.2378 (8) | 0.5079 (9) | 0.3865 (7) | 0.046 (2) | |
H6 | −0.3245 | 0.5383 | 0.3998 | 0.055* | |
C7 | −0.1423 (8) | 0.5774 (8) | 0.3765 (7) | 0.038 (2) | |
C8 | −0.1693 (9) | 0.6931 (8) | 0.3880 (7) | 0.048 (2) | |
H8 | −0.2541 | 0.7286 | 0.4015 | 0.057* | |
C9 | −0.0698 (9) | 0.7508 (8) | 0.3791 (7) | 0.048 (2) | |
H9 | −0.0864 | 0.8260 | 0.3875 | 0.058* | |
C10 | 0.0576 (8) | 0.6983 (7) | 0.3574 (6) | 0.039 (2) | |
H10 | 0.1239 | 0.7401 | 0.3512 | 0.046* | |
C11 | −0.0122 (8) | 0.5335 (7) | 0.3539 (6) | 0.034 (2) | |
C12 | 0.0227 (8) | 0.4161 (7) | 0.3447 (6) | 0.035 (2) | |
C13 | 0.2288 (9) | 0.4915 (8) | 0.0490 (8) | 0.048 (2) | |
H13 | 0.1739 | 0.4380 | 0.0769 | 0.057* | |
C14 | 0.2591 (10) | 0.5203 (8) | −0.0624 (8) | 0.054 (3) | |
H14 | 0.2226 | 0.4888 | −0.1088 | 0.064* | |
C15 | 0.3433 (10) | 0.5956 (8) | −0.1063 (8) | 0.054 (3) | |
H15 | 0.3644 | 0.6154 | −0.1823 | 0.064* | |
C16 | 0.3972 (8) | 0.6426 (7) | −0.0350 (7) | 0.038 (2) | |
C17 | 0.4883 (8) | 0.7207 (7) | −0.0708 (8) | 0.046 (3) | |
H17 | 0.5168 | 0.7401 | −0.1451 | 0.056* | |
C18 | 0.5329 (8) | 0.7659 (8) | 0.0002 (9) | 0.053 (3) | |
H18 | 0.5907 | 0.8170 | −0.0260 | 0.064* | |
C19 | 0.4928 (8) | 0.7367 (7) | 0.1173 (7) | 0.035 (2) | |
C20 | 0.5310 (8) | 0.7839 (7) | 0.1950 (8) | 0.045 (2) | |
H20 | 0.5872 | 0.8368 | 0.1729 | 0.054* | |
C21 | 0.4872 (8) | 0.7537 (7) | 0.3016 (8) | 0.043 (2) | |
H21 | 0.5120 | 0.7863 | 0.3530 | 0.052* | |
C22 | 0.4039 (8) | 0.6726 (7) | 0.3347 (7) | 0.038 (2) | |
H22 | 0.3767 | 0.6500 | 0.4093 | 0.046* | |
C23 | 0.4074 (7) | 0.6591 (6) | 0.1547 (7) | 0.030 (2) | |
C24 | 0.3590 (7) | 0.6110 (7) | 0.0794 (7) | 0.034 (2) | |
C25 | 0.2579 (9) | 0.9594 (8) | 0.7577 (8) | 0.049 (3) | |
C26 | 0.1954 (7) | 0.9226 (7) | 0.8720 (7) | 0.031 (2) | |
C27 | 0.2286 (7) | 0.9577 (7) | 0.9605 (7) | 0.034 (2) | |
H27 | 0.2916 | 1.0039 | 0.9482 | 0.041* | |
C28 | 0.1708 (8) | 0.9259 (7) | 1.0669 (6) | 0.032 (2) | |
C29 | 0.0764 (7) | 0.8577 (7) | 1.0848 (7) | 0.033 (2) | |
H29 | 0.0349 | 0.8370 | 1.1545 | 0.039* | |
C30 | 0.0442 (7) | 0.8208 (6) | 0.9982 (7) | 0.0303 (19) | |
C31 | 0.1027 (7) | 0.8533 (7) | 0.8921 (7) | 0.034 (2) | |
H31 | 0.0790 | 0.8282 | 0.8348 | 0.041* | |
C32 | 0.2090 (9) | 0.9603 (7) | 1.1632 (7) | 0.037 (2) | |
H7A | 0.379 (7) | 0.039 (6) | 0.246 (3) | 0.044* | |
H7B | 0.413 (8) | 0.007 (6) | 0.362 (2) | 0.044* | |
H8A | 0.329 (6) | 0.935 (6) | 0.551 (5) | 0.044* | |
H8B | 0.433 (6) | 0.847 (5) | 0.525 (5) | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0239 (6) | 0.0319 (6) | 0.0384 (6) | −0.0132 (4) | 0.0053 (4) | −0.0117 (5) |
Cl1 | 0.0337 (13) | 0.0452 (14) | 0.0684 (18) | −0.0045 (11) | −0.0058 (12) | −0.0089 (12) |
O1 | 0.096 (6) | 0.143 (7) | 0.063 (5) | −0.086 (6) | 0.038 (4) | −0.068 (5) |
O2 | 0.036 (4) | 0.065 (4) | 0.057 (4) | −0.017 (3) | 0.015 (4) | −0.024 (4) |
O3 | 0.072 (5) | 0.052 (4) | 0.046 (4) | −0.045 (4) | 0.007 (3) | −0.015 (3) |
O4 | 0.058 (4) | 0.061 (4) | 0.038 (4) | −0.035 (3) | 0.009 (3) | −0.019 (3) |
O5 | 0.125 (7) | 0.123 (7) | 0.074 (6) | −0.093 (6) | 0.013 (5) | −0.044 (5) |
O6 | 0.113 (7) | 0.137 (7) | 0.054 (5) | −0.099 (6) | 0.030 (5) | −0.027 (5) |
O7 | 0.057 (4) | 0.063 (5) | 0.047 (4) | −0.019 (4) | −0.004 (4) | −0.026 (4) |
O8 | 0.126 (9) | 0.202 (12) | 0.057 (6) | 0.044 (8) | 0.021 (6) | −0.028 (7) |
N1 | 0.031 (4) | 0.036 (4) | 0.039 (4) | −0.020 (3) | 0.009 (3) | −0.013 (3) |
N2 | 0.030 (4) | 0.028 (4) | 0.034 (4) | −0.006 (3) | 0.001 (3) | −0.009 (3) |
N3 | 0.036 (4) | 0.037 (4) | 0.046 (5) | −0.020 (3) | 0.001 (3) | −0.019 (4) |
N4 | 0.032 (4) | 0.035 (4) | 0.034 (4) | −0.012 (3) | −0.001 (3) | −0.015 (3) |
N5 | 0.055 (6) | 0.065 (6) | 0.050 (6) | −0.033 (5) | −0.001 (5) | −0.016 (5) |
C1 | 0.041 (6) | 0.051 (6) | 0.052 (6) | −0.017 (5) | 0.005 (5) | −0.021 (5) |
C2 | 0.063 (7) | 0.059 (7) | 0.065 (7) | −0.036 (6) | 0.013 (6) | −0.039 (6) |
C3 | 0.049 (6) | 0.072 (7) | 0.034 (6) | −0.036 (6) | 0.012 (5) | −0.019 (5) |
C4 | 0.034 (5) | 0.051 (6) | 0.022 (5) | −0.022 (4) | −0.001 (4) | −0.009 (4) |
C5 | 0.040 (6) | 0.064 (7) | 0.043 (6) | −0.027 (5) | −0.007 (5) | −0.010 (5) |
C6 | 0.021 (5) | 0.075 (7) | 0.037 (6) | −0.011 (5) | −0.003 (4) | −0.006 (5) |
C7 | 0.030 (5) | 0.048 (6) | 0.031 (5) | −0.010 (4) | 0.001 (4) | −0.003 (4) |
C8 | 0.040 (6) | 0.061 (7) | 0.036 (6) | −0.002 (5) | 0.002 (4) | −0.010 (5) |
C9 | 0.059 (7) | 0.044 (6) | 0.040 (6) | −0.003 (5) | 0.007 (5) | −0.016 (5) |
C10 | 0.038 (5) | 0.042 (6) | 0.032 (5) | −0.006 (4) | 0.005 (4) | −0.007 (4) |
C11 | 0.037 (5) | 0.042 (5) | 0.021 (5) | −0.002 (4) | −0.007 (4) | −0.006 (4) |
C12 | 0.043 (6) | 0.046 (6) | 0.021 (5) | −0.022 (5) | −0.001 (4) | −0.006 (4) |
C13 | 0.054 (6) | 0.052 (6) | 0.045 (6) | −0.014 (5) | 0.011 (5) | −0.026 (5) |
C14 | 0.070 (7) | 0.055 (7) | 0.044 (6) | −0.005 (6) | −0.012 (5) | −0.029 (5) |
C15 | 0.081 (8) | 0.049 (6) | 0.028 (5) | −0.005 (6) | −0.005 (5) | −0.008 (5) |
C16 | 0.041 (5) | 0.028 (5) | 0.038 (5) | 0.004 (4) | 0.005 (4) | −0.008 (4) |
C17 | 0.043 (6) | 0.040 (6) | 0.046 (6) | −0.009 (5) | 0.021 (5) | −0.001 (5) |
C18 | 0.034 (6) | 0.047 (6) | 0.074 (8) | −0.020 (5) | 0.019 (5) | −0.009 (5) |
C19 | 0.030 (5) | 0.025 (5) | 0.045 (6) | −0.007 (4) | 0.005 (4) | −0.003 (4) |
C20 | 0.045 (6) | 0.036 (5) | 0.054 (7) | −0.019 (5) | 0.002 (5) | −0.007 (5) |
C21 | 0.032 (5) | 0.035 (5) | 0.074 (7) | −0.005 (4) | −0.008 (5) | −0.031 (5) |
C22 | 0.039 (5) | 0.037 (5) | 0.041 (6) | −0.013 (4) | −0.003 (4) | −0.012 (4) |
C23 | 0.027 (5) | 0.022 (4) | 0.044 (6) | −0.005 (4) | −0.003 (4) | −0.013 (4) |
C24 | 0.023 (5) | 0.032 (5) | 0.043 (6) | 0.007 (4) | 0.004 (4) | −0.012 (4) |
C25 | 0.035 (6) | 0.066 (7) | 0.055 (7) | −0.026 (5) | 0.010 (5) | −0.024 (5) |
C26 | 0.029 (5) | 0.030 (5) | 0.037 (5) | −0.011 (4) | 0.005 (4) | −0.012 (4) |
C27 | 0.024 (5) | 0.033 (5) | 0.045 (6) | −0.006 (4) | −0.005 (4) | −0.010 (4) |
C28 | 0.040 (5) | 0.034 (5) | 0.026 (5) | −0.016 (4) | 0.005 (4) | −0.008 (4) |
C29 | 0.022 (4) | 0.037 (5) | 0.034 (5) | −0.003 (4) | 0.002 (4) | −0.004 (4) |
C30 | 0.032 (5) | 0.026 (5) | 0.034 (5) | −0.011 (4) | 0.000 (4) | −0.007 (4) |
C31 | 0.028 (5) | 0.039 (5) | 0.046 (6) | −0.014 (4) | 0.001 (4) | −0.021 (4) |
C32 | 0.050 (6) | 0.028 (5) | 0.035 (6) | −0.009 (4) | −0.003 (5) | −0.011 (4) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.002 (6) | C7—C8 | 1.424 (11) |
Cu1—N4 | 2.002 (6) | C8—C9 | 1.356 (11) |
Cu1—N2 | 2.082 (6) | C8—H8 | 0.9300 |
Cu1—N3 | 2.168 (7) | C9—C10 | 1.399 (11) |
Cu1—Cl1 | 2.287 (2) | C9—H9 | 0.9300 |
O1—C25 | 1.225 (10) | C10—H10 | 0.9300 |
O2—C25 | 1.251 (9) | C11—C12 | 1.435 (11) |
O2—H2A | 0.8200 | C13—C14 | 1.361 (11) |
O3—C32 | 1.312 (9) | C13—H13 | 0.9300 |
O4—C32 | 1.192 (9) | C14—C15 | 1.371 (12) |
O5—N5 | 1.199 (9) | C14—H14 | 0.9300 |
O6—N5 | 1.205 (9) | C15—C16 | 1.404 (11) |
O7—H7A | 0.805 (19) | C15—H15 | 0.9300 |
O7—H7B | 0.796 (19) | C16—C24 | 1.415 (11) |
O8—H8A | 0.83 (2) | C16—C17 | 1.439 (11) |
O8—H8B | 0.82 (2) | C17—C18 | 1.335 (12) |
N1—C1 | 1.330 (10) | C17—H17 | 0.9300 |
N1—C12 | 1.359 (10) | C18—C19 | 1.451 (12) |
N2—C10 | 1.307 (9) | C18—H18 | 0.9300 |
N2—C11 | 1.363 (9) | C19—C20 | 1.389 (11) |
N3—C13 | 1.357 (10) | C19—C23 | 1.391 (10) |
N3—C24 | 1.362 (9) | C20—C21 | 1.343 (11) |
N4—C22 | 1.321 (9) | C20—H20 | 0.9300 |
N4—C23 | 1.373 (9) | C21—C22 | 1.402 (10) |
N5—C30 | 1.465 (10) | C21—H21 | 0.9300 |
C1—C2 | 1.375 (11) | C22—H22 | 0.9300 |
C1—H1 | 0.9300 | C23—C24 | 1.423 (10) |
C2—C3 | 1.381 (12) | C25—C26 | 1.504 (11) |
C2—H2 | 0.9300 | C26—C31 | 1.377 (10) |
C3—C4 | 1.405 (11) | C26—C27 | 1.395 (10) |
C3—H3A | 0.9300 | C27—C28 | 1.396 (10) |
C4—C12 | 1.381 (10) | C27—H27 | 0.9300 |
C4—C5 | 1.429 (11) | C28—C29 | 1.384 (10) |
C5—C6 | 1.358 (11) | C28—C32 | 1.499 (11) |
C5—H5 | 0.9300 | C29—C30 | 1.382 (10) |
C6—C7 | 1.417 (11) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—C31 | 1.397 (10) |
C7—C11 | 1.397 (11) | C31—H31 | 0.9300 |
| | | |
N1—Cu1—N4 | 174.6 (3) | N1—C12—C11 | 116.4 (7) |
N1—Cu1—N2 | 81.0 (3) | C4—C12—C11 | 120.5 (8) |
N4—Cu1—N2 | 97.1 (2) | N3—C13—C14 | 123.5 (9) |
N1—Cu1—N3 | 96.3 (2) | N3—C13—H13 | 118.3 |
N4—Cu1—N3 | 79.4 (2) | C14—C13—H13 | 118.3 |
N2—Cu1—N3 | 108.1 (2) | C13—C14—C15 | 120.2 (9) |
N1—Cu1—Cl1 | 94.8 (2) | C13—C14—H14 | 119.9 |
N4—Cu1—Cl1 | 89.93 (19) | C15—C14—H14 | 119.9 |
N2—Cu1—Cl1 | 139.31 (19) | C14—C15—C16 | 119.1 (9) |
N3—Cu1—Cl1 | 112.61 (19) | C14—C15—H15 | 120.5 |
C25—O2—H2A | 109.5 | C16—C15—H15 | 120.5 |
H7A—O7—H7B | 131 (4) | C15—C16—C24 | 117.7 (8) |
H8A—O8—H8B | 123 (4) | C15—C16—C17 | 124.3 (9) |
C1—N1—C12 | 117.6 (7) | C24—C16—C17 | 118.1 (8) |
C1—N1—Cu1 | 128.4 (6) | C18—C17—C16 | 121.6 (8) |
C12—N1—Cu1 | 114.0 (5) | C18—C17—H17 | 119.2 |
C10—N2—C11 | 117.8 (7) | C16—C17—H17 | 119.2 |
C10—N2—Cu1 | 131.1 (6) | C17—C18—C19 | 121.2 (8) |
C11—N2—Cu1 | 111.0 (5) | C17—C18—H18 | 119.4 |
C13—N3—C24 | 117.0 (7) | C19—C18—H18 | 119.4 |
C13—N3—Cu1 | 132.6 (6) | C20—C19—C23 | 117.2 (8) |
C24—N3—Cu1 | 109.8 (5) | C20—C19—C18 | 124.4 (8) |
C22—N4—C23 | 117.8 (7) | C23—C19—C18 | 118.4 (8) |
C22—N4—Cu1 | 126.4 (6) | C21—C20—C19 | 120.5 (8) |
C23—N4—Cu1 | 115.2 (5) | C21—C20—H20 | 119.7 |
O5—N5—O6 | 123.7 (8) | C19—C20—H20 | 119.7 |
O5—N5—C30 | 118.5 (8) | C20—C21—C22 | 119.5 (8) |
O6—N5—C30 | 117.7 (8) | C20—C21—H21 | 120.2 |
N1—C1—C2 | 123.7 (9) | C22—C21—H21 | 120.2 |
N1—C1—H1 | 118.2 | N4—C22—C21 | 122.2 (8) |
C2—C1—H1 | 118.2 | N4—C22—H22 | 118.9 |
C1—C2—C3 | 118.7 (9) | C21—C22—H22 | 118.9 |
C1—C2—H2 | 120.6 | N4—C23—C19 | 122.7 (7) |
C3—C2—H2 | 120.6 | N4—C23—C24 | 116.6 (7) |
C2—C3—C4 | 119.1 (8) | C19—C23—C24 | 120.7 (8) |
C2—C3—H3A | 120.4 | N3—C24—C16 | 122.5 (8) |
C4—C3—H3A | 120.4 | N3—C24—C23 | 117.5 (7) |
C12—C4—C3 | 117.8 (8) | C16—C24—C23 | 120.0 (8) |
C12—C4—C5 | 119.2 (8) | O1—C25—O2 | 125.8 (9) |
C3—C4—C5 | 123.0 (8) | O1—C25—C26 | 117.8 (8) |
C6—C5—C4 | 120.8 (8) | O2—C25—C26 | 116.4 (8) |
C6—C5—H5 | 119.6 | C31—C26—C27 | 117.9 (7) |
C4—C5—H5 | 119.6 | C31—C26—C25 | 120.7 (8) |
C5—C6—C7 | 120.5 (8) | C27—C26—C25 | 121.4 (7) |
C5—C6—H6 | 119.8 | C26—C27—C28 | 122.4 (8) |
C7—C6—H6 | 119.8 | C26—C27—H27 | 118.8 |
C11—C7—C6 | 120.2 (8) | C28—C27—H27 | 118.8 |
C11—C7—C8 | 115.8 (8) | C29—C28—C27 | 118.7 (7) |
C6—C7—C8 | 124.0 (8) | C29—C28—C32 | 118.6 (7) |
C9—C8—C7 | 119.0 (8) | C27—C28—C32 | 122.6 (7) |
C9—C8—H8 | 120.5 | C30—C29—C28 | 119.4 (7) |
C7—C8—H8 | 120.5 | C30—C29—H29 | 120.3 |
C8—C9—C10 | 120.7 (9) | C28—C29—H29 | 120.3 |
C8—C9—H9 | 119.7 | C29—C30—C31 | 121.3 (7) |
C10—C9—H9 | 119.7 | C29—C30—N5 | 120.3 (7) |
N2—C10—C9 | 122.3 (8) | C31—C30—N5 | 118.4 (7) |
N2—C10—H10 | 118.8 | C26—C31—C30 | 120.2 (8) |
C9—C10—H10 | 118.8 | C26—C31—H31 | 119.9 |
N2—C11—C7 | 124.4 (8) | C30—C31—H31 | 119.9 |
N2—C11—C12 | 116.8 (7) | O4—C32—O3 | 124.0 (8) |
C7—C11—C12 | 118.7 (8) | O4—C32—C28 | 122.4 (8) |
N1—C12—C4 | 123.0 (8) | O3—C32—C28 | 113.6 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8B···Cl1i | 0.82 (6) | 2.64 (4) | 3.420 (10) | 160 (8) |
O8—H8A···O1 | 0.83 (7) | 1.90 (5) | 2.642 (10) | 149 (8) |
O7—H7B···O8ii | 0.80 (3) | 1.95 (3) | 2.718 (11) | 163 (7) |
O7—H7A···O3iii | 0.80 (5) | 1.73 (6) | 2.526 (8) | 176 (8) |
O2—H2A···O7i | 0.82 | 1.94 | 2.651 (9) | 145 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x, y−1, z−1. |