The drug norfloxacin and ligand 2,2'-bipyridine coordinate to copper(II) yielding a mixed-ligand complex, [Cu(C16H18FN3O3)(NO3)(C10H8N2)](NO3)·2H2O or [Cu(H-Norf)(NO3)(bpy)](NO3)·2H2O. The CuII atom has a five-coordinate environment with square-based pyramidal geometry, which involves two N atoms from the 2,2'-bipyridine ligand, two O atoms from the norfloxacinate ligand and one nitrate O atom. Weak interactions between O and Cu result in a centrosymmetric dimer.
Supporting information
CCDC reference: 262241
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.080
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.07 Ratio
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.03
PLAT213_ALERT_2_C Atom O6 has ADP max/min Ratio ............. 3.10 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N6 .. 6.28 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N6 .. 6.31 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O4 .. 5.70 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O8 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N7 .. 2.70 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; 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); software used to prepare material for publication: SHELXL97.
(2,2'-bipyridine)[1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-4-ium-
1-yl)quinoline-3-carboxylato]nitratocopper(II) nitrate dihydrate
top
Crystal data top
[Cu(C16H18FN3O3)(NO3)(C10H8N2)](NO3)·2H2O | F(000) = 1444 |
Mr = 699.12 | Dx = 1.668 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6954 reflections |
a = 13.9080 (8) Å | θ = 1.5–25.0° |
b = 13.8441 (8) Å | µ = 0.87 mm−1 |
c = 14.4835 (9) Å | T = 130 K |
β = 93.173 (3)° | Prism, blue |
V = 2784.4 (3) Å3 | 0.32 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku Mercury CCD diffractometer | 4902 independent reflections |
Radiation source: RX | 4561 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (Blessing, 1995) | h = −16→15 |
Tmin = 0.770, Tmax = 0.852 | k = −16→16 |
17478 measured reflections | l = −16→17 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0385P)2 + 2.0954P] where P = (Fo2 + 2Fc2)/3 |
4902 reflections | (Δ/σ)max = 0.001 |
428 parameters | Δρmax = 0.44 e Å−3 |
6 restraints | Δρmin = −0.29 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 | |
Cu | 0.562304 (17) | 0.619036 (18) | 0.478556 (17) | 0.01392 (9) | |
O1 | 0.62037 (10) | 0.53634 (11) | 0.22056 (10) | 0.0183 (3) | |
O2 | 0.61922 (10) | 0.57102 (10) | 0.36969 (10) | 0.0170 (3) | |
O3 | 0.43599 (10) | 0.57074 (10) | 0.44121 (10) | 0.0161 (3) | |
O4 | 0.52470 (12) | 0.76620 (11) | 0.40022 (12) | 0.0280 (4) | |
O5 | 0.45063 (15) | 0.87282 (15) | 0.48047 (15) | 0.0457 (5) | |
O6 | 0.60499 (15) | 0.87512 (15) | 0.4789 (2) | 0.0655 (8) | |
O7 | 0.58529 (15) | 0.70766 (15) | −0.00621 (16) | 0.0507 (6) | |
O8 | 0.71344 (12) | 0.75584 (14) | 0.07310 (14) | 0.0371 (5) | |
O9 | 0.57868 (13) | 0.74306 (14) | 0.13846 (15) | 0.0416 (5) | |
O10 | 0.69350 (13) | 0.78801 (15) | 0.30013 (15) | 0.0400 (5) | |
H3 | 0.652 (2) | 0.782 (2) | 0.3414 (16) | 0.060* | |
H4 | 0.672 (2) | 0.763 (2) | 0.2495 (14) | 0.060* | |
O11 | 0.22285 (15) | 0.30834 (17) | 0.10471 (13) | 0.0441 (5) | |
H1 | 0.1639 (13) | 0.315 (3) | 0.088 (2) | 0.066* | |
H2 | 0.253 (2) | 0.293 (3) | 0.0567 (18) | 0.066* | |
F | 0.08296 (8) | 0.56467 (10) | 0.45241 (9) | 0.0228 (3) | |
N1 | 0.52094 (12) | 0.65893 (12) | 0.60288 (12) | 0.0150 (4) | |
N2 | 0.68982 (12) | 0.66130 (12) | 0.53459 (12) | 0.0147 (4) | |
N3 | 0.33287 (12) | 0.55211 (12) | 0.17020 (12) | 0.0134 (4) | |
N4 | 0.00350 (12) | 0.54694 (12) | 0.27594 (12) | 0.0144 (4) | |
N5 | −0.19135 (12) | 0.49231 (13) | 0.22420 (13) | 0.0170 (4) | |
H5A | −0.2546 | 0.5056 | 0.2259 | 0.020* | |
H5B | −0.1853 | 0.4372 | 0.1921 | 0.020* | |
N6 | 0.52750 (16) | 0.83850 (15) | 0.45415 (15) | 0.0310 (5) | |
N7 | 0.62535 (14) | 0.73499 (14) | 0.06818 (17) | 0.0305 (5) | |
C | 0.57650 (14) | 0.55691 (14) | 0.29068 (15) | 0.0140 (4) | |
C1 | 0.43070 (15) | 0.66242 (15) | 0.62983 (15) | 0.0174 (4) | |
H1A | 0.3802 | 0.6512 | 0.5863 | 0.021* | |
C2 | 0.40970 (15) | 0.68210 (15) | 0.72017 (16) | 0.0200 (5) | |
H2A | 0.3462 | 0.6847 | 0.7371 | 0.024* | |
C3 | 0.48510 (16) | 0.69787 (16) | 0.78483 (16) | 0.0210 (5) | |
H3A | 0.4728 | 0.7096 | 0.8463 | 0.025* | |
C4 | 0.57916 (16) | 0.69613 (15) | 0.75753 (16) | 0.0197 (5) | |
H4A | 0.6306 | 0.7070 | 0.8001 | 0.024* | |
C5 | 0.59483 (14) | 0.67778 (14) | 0.66552 (15) | 0.0154 (4) | |
C6 | 0.69033 (14) | 0.67995 (14) | 0.62599 (15) | 0.0152 (4) | |
C7 | 0.77532 (15) | 0.70300 (15) | 0.67701 (16) | 0.0181 (5) | |
H7 | 0.7754 | 0.7136 | 0.7404 | 0.022* | |
C8 | 0.85931 (15) | 0.70970 (15) | 0.63089 (17) | 0.0212 (5) | |
H8 | 0.9169 | 0.7249 | 0.6633 | 0.025* | |
C9 | 0.85797 (15) | 0.69385 (15) | 0.53655 (16) | 0.0211 (5) | |
H9 | 0.9140 | 0.6994 | 0.5047 | 0.025* | |
C10 | 0.77136 (15) | 0.66953 (15) | 0.49036 (16) | 0.0178 (5) | |
H10 | 0.7699 | 0.6586 | 0.4269 | 0.021* | |
C11 | 0.40758 (14) | 0.56619 (14) | 0.35561 (14) | 0.0127 (4) | |
C12 | 0.46850 (14) | 0.56168 (14) | 0.28045 (14) | 0.0135 (4) | |
C13 | 0.42764 (14) | 0.55474 (14) | 0.19178 (15) | 0.0136 (4) | |
H13 | 0.4689 | 0.5517 | 0.1435 | 0.016* | |
C14 | 0.29396 (15) | 0.54690 (17) | 0.07233 (15) | 0.0192 (5) | |
H14A | 0.2545 | 0.6035 | 0.0592 | 0.023* | |
H14B | 0.2526 | 0.4907 | 0.0654 | 0.023* | |
C15 | 0.36985 (16) | 0.54099 (18) | 0.00173 (16) | 0.0245 (5) | |
H15A | 0.4120 | 0.5958 | 0.0085 | 0.037* | |
H15B | 0.3393 | 0.5408 | −0.0594 | 0.037* | |
H15C | 0.4065 | 0.4827 | 0.0112 | 0.037* | |
C16 | 0.26802 (14) | 0.55496 (14) | 0.24086 (15) | 0.0132 (4) | |
C17 | 0.16791 (14) | 0.55027 (14) | 0.22062 (15) | 0.0146 (4) | |
H17 | 0.1443 | 0.5467 | 0.1594 | 0.018* | |
C18 | 0.10407 (14) | 0.55093 (14) | 0.29101 (15) | 0.0140 (4) | |
C19 | 0.14420 (14) | 0.55912 (15) | 0.38257 (15) | 0.0156 (4) | |
C20 | 0.23995 (14) | 0.56389 (14) | 0.40378 (15) | 0.0145 (4) | |
H20 | 0.2628 | 0.5689 | 0.4652 | 0.017* | |
C21 | 0.30505 (14) | 0.56131 (14) | 0.33281 (14) | 0.0136 (4) | |
C22 | −0.03389 (14) | 0.55877 (16) | 0.18016 (15) | 0.0180 (5) | |
H22A | −0.0180 | 0.5022 | 0.1445 | 0.022* | |
H22B | −0.0039 | 0.6145 | 0.1530 | 0.022* | |
C23 | −0.14260 (15) | 0.57235 (16) | 0.17615 (16) | 0.0206 (5) | |
H23A | −0.1578 | 0.6333 | 0.2049 | 0.025* | |
H23B | −0.1667 | 0.5748 | 0.1121 | 0.025* | |
C24 | −0.14969 (14) | 0.47853 (16) | 0.32014 (15) | 0.0193 (5) | |
H24A | −0.1793 | 0.4230 | 0.3480 | 0.023* | |
H24B | −0.1626 | 0.5350 | 0.3571 | 0.023* | |
C25 | −0.04228 (14) | 0.46305 (15) | 0.31838 (15) | 0.0175 (5) | |
H25A | −0.0152 | 0.4541 | 0.3810 | 0.021* | |
H25B | −0.0295 | 0.4052 | 0.2833 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.00881 (14) | 0.01823 (15) | 0.01447 (15) | −0.00076 (9) | −0.00171 (10) | −0.00140 (10) |
O1 | 0.0107 (7) | 0.0280 (8) | 0.0164 (8) | 0.0018 (6) | 0.0013 (6) | −0.0020 (6) |
O2 | 0.0104 (7) | 0.0242 (8) | 0.0163 (8) | 0.0008 (6) | −0.0008 (6) | −0.0029 (6) |
O3 | 0.0113 (7) | 0.0226 (8) | 0.0142 (8) | −0.0025 (6) | −0.0010 (6) | 0.0005 (6) |
O4 | 0.0365 (10) | 0.0202 (8) | 0.0265 (10) | −0.0017 (7) | −0.0055 (7) | −0.0019 (7) |
O5 | 0.0428 (12) | 0.0521 (13) | 0.0425 (12) | −0.0001 (10) | 0.0063 (9) | −0.0209 (10) |
O6 | 0.0395 (12) | 0.0416 (12) | 0.110 (2) | 0.0047 (9) | −0.0451 (13) | −0.0234 (12) |
O7 | 0.0402 (11) | 0.0486 (12) | 0.0611 (15) | −0.0008 (9) | −0.0181 (10) | −0.0166 (11) |
O8 | 0.0169 (9) | 0.0499 (11) | 0.0444 (12) | −0.0032 (8) | 0.0008 (8) | −0.0048 (9) |
O9 | 0.0242 (10) | 0.0387 (11) | 0.0631 (14) | 0.0042 (8) | 0.0141 (9) | −0.0007 (10) |
O10 | 0.0277 (10) | 0.0478 (12) | 0.0443 (12) | −0.0063 (8) | −0.0004 (9) | 0.0242 (10) |
O11 | 0.0400 (12) | 0.0631 (14) | 0.0285 (11) | 0.0060 (10) | −0.0030 (9) | −0.0052 (10) |
F | 0.0129 (6) | 0.0399 (8) | 0.0159 (7) | −0.0028 (5) | 0.0040 (5) | −0.0045 (6) |
N1 | 0.0135 (9) | 0.0135 (8) | 0.0178 (10) | 0.0000 (7) | −0.0002 (7) | −0.0007 (7) |
N2 | 0.0118 (9) | 0.0137 (8) | 0.0184 (10) | 0.0000 (7) | −0.0017 (7) | −0.0005 (7) |
N3 | 0.0100 (8) | 0.0160 (9) | 0.0140 (9) | 0.0003 (6) | −0.0006 (7) | 0.0005 (7) |
N4 | 0.0096 (8) | 0.0174 (9) | 0.0161 (9) | −0.0012 (7) | −0.0003 (7) | 0.0016 (7) |
N5 | 0.0064 (8) | 0.0191 (9) | 0.0254 (10) | 0.0003 (7) | −0.0003 (7) | −0.0011 (8) |
N6 | 0.0383 (13) | 0.0243 (11) | 0.0287 (12) | −0.0009 (9) | −0.0141 (10) | 0.0043 (9) |
N7 | 0.0225 (11) | 0.0225 (10) | 0.0465 (14) | 0.0053 (8) | 0.0008 (10) | −0.0004 (10) |
C | 0.0115 (10) | 0.0129 (10) | 0.0173 (11) | 0.0012 (7) | −0.0018 (8) | 0.0002 (8) |
C1 | 0.0136 (10) | 0.0152 (10) | 0.0232 (12) | −0.0014 (8) | −0.0016 (9) | −0.0004 (9) |
C2 | 0.0150 (11) | 0.0172 (11) | 0.0283 (13) | 0.0002 (8) | 0.0041 (9) | −0.0022 (9) |
C3 | 0.0265 (12) | 0.0198 (11) | 0.0169 (12) | 0.0010 (9) | 0.0041 (9) | −0.0025 (9) |
C4 | 0.0195 (11) | 0.0192 (11) | 0.0198 (12) | −0.0003 (8) | −0.0033 (9) | −0.0036 (9) |
C5 | 0.0144 (10) | 0.0107 (10) | 0.0207 (12) | 0.0000 (8) | −0.0026 (8) | −0.0006 (8) |
C6 | 0.0152 (10) | 0.0107 (10) | 0.0191 (12) | 0.0013 (8) | −0.0035 (8) | 0.0008 (8) |
C7 | 0.0178 (11) | 0.0171 (10) | 0.0187 (12) | 0.0009 (8) | −0.0052 (9) | −0.0023 (9) |
C8 | 0.0132 (11) | 0.0173 (11) | 0.0322 (14) | −0.0004 (8) | −0.0066 (9) | −0.0008 (10) |
C9 | 0.0138 (11) | 0.0201 (11) | 0.0294 (13) | 0.0000 (8) | 0.0007 (9) | 0.0029 (9) |
C10 | 0.0148 (11) | 0.0175 (11) | 0.0212 (12) | 0.0013 (8) | 0.0007 (9) | −0.0001 (9) |
C11 | 0.0133 (10) | 0.0103 (9) | 0.0142 (11) | −0.0009 (7) | −0.0024 (8) | 0.0010 (8) |
C12 | 0.0093 (10) | 0.0135 (10) | 0.0177 (11) | −0.0003 (7) | −0.0004 (8) | −0.0011 (8) |
C13 | 0.0108 (10) | 0.0145 (10) | 0.0159 (11) | 0.0008 (8) | 0.0029 (8) | 0.0002 (8) |
C14 | 0.0146 (11) | 0.0284 (12) | 0.0142 (11) | 0.0005 (9) | −0.0023 (8) | −0.0017 (9) |
C15 | 0.0159 (11) | 0.0418 (14) | 0.0156 (12) | −0.0006 (10) | −0.0006 (9) | −0.0040 (10) |
C16 | 0.0114 (10) | 0.0124 (10) | 0.0156 (11) | −0.0010 (7) | 0.0006 (8) | 0.0007 (8) |
C17 | 0.0133 (10) | 0.0161 (10) | 0.0143 (11) | −0.0004 (8) | −0.0016 (8) | −0.0010 (8) |
C18 | 0.0110 (10) | 0.0111 (9) | 0.0197 (11) | −0.0002 (7) | −0.0006 (8) | 0.0012 (8) |
C19 | 0.0123 (10) | 0.0190 (11) | 0.0160 (11) | −0.0004 (8) | 0.0049 (8) | −0.0007 (8) |
C20 | 0.0144 (10) | 0.0159 (10) | 0.0130 (11) | −0.0004 (8) | −0.0017 (8) | −0.0016 (8) |
C21 | 0.0129 (10) | 0.0105 (10) | 0.0172 (11) | −0.0008 (7) | −0.0003 (8) | 0.0005 (8) |
C22 | 0.0119 (10) | 0.0230 (11) | 0.0188 (12) | −0.0010 (8) | −0.0009 (8) | 0.0016 (9) |
C23 | 0.0130 (11) | 0.0244 (12) | 0.0241 (13) | −0.0003 (8) | −0.0021 (9) | 0.0046 (10) |
C24 | 0.0113 (10) | 0.0253 (12) | 0.0214 (12) | −0.0024 (8) | 0.0013 (8) | 0.0025 (9) |
C25 | 0.0113 (10) | 0.0202 (11) | 0.0209 (12) | −0.0016 (8) | −0.0008 (8) | 0.0027 (9) |
Geometric parameters (Å, º) top
Cu—O2 | 1.9217 (15) | C4—C5 | 1.386 (3) |
Cu—O3 | 1.9289 (14) | C4—H4A | 0.9300 |
Cu—N2 | 1.9967 (17) | C5—C6 | 1.475 (3) |
Cu—N1 | 1.9983 (18) | C6—C7 | 1.396 (3) |
Cu—O4 | 2.3760 (16) | C7—C8 | 1.381 (3) |
O1—C | 1.246 (3) | C7—H7 | 0.9300 |
O2—C | 1.275 (2) | C8—C9 | 1.383 (3) |
O3—C11 | 1.282 (2) | C8—H8 | 0.9300 |
O4—N6 | 1.269 (3) | C9—C10 | 1.387 (3) |
O5—N6 | 1.249 (3) | C9—H9 | 0.9300 |
O6—N6 | 1.226 (3) | C10—H10 | 0.9300 |
O7—N7 | 1.244 (3) | C11—C12 | 1.417 (3) |
O8—N7 | 1.257 (3) | C11—C21 | 1.447 (3) |
O9—N7 | 1.242 (3) | C12—C13 | 1.379 (3) |
O10—H3 | 0.857 (17) | C13—H13 | 0.9300 |
O10—H4 | 0.847 (17) | C14—C15 | 1.512 (3) |
O11—H1 | 0.848 (17) | C14—H14A | 0.9700 |
O11—H2 | 0.858 (17) | C14—H14B | 0.9700 |
F—C19 | 1.360 (2) | C15—H15A | 0.9600 |
N1—C1 | 1.336 (3) | C15—H15B | 0.9600 |
N1—C5 | 1.358 (3) | C15—H15C | 0.9600 |
N2—C10 | 1.338 (3) | C16—C21 | 1.404 (3) |
N2—C6 | 1.348 (3) | C16—C17 | 1.408 (3) |
N3—C13 | 1.338 (3) | C17—C18 | 1.388 (3) |
N3—C16 | 1.402 (3) | C17—H17 | 0.9300 |
N3—C14 | 1.491 (3) | C18—C19 | 1.414 (3) |
N4—C18 | 1.405 (3) | C19—C20 | 1.352 (3) |
N4—C22 | 1.463 (3) | C20—C21 | 1.407 (3) |
N4—C25 | 1.475 (3) | C20—H20 | 0.9300 |
N5—C24 | 1.488 (3) | C22—C23 | 1.522 (3) |
N5—C23 | 1.491 (3) | C22—H22A | 0.9700 |
N5—H5A | 0.9000 | C22—H22B | 0.9700 |
N5—H5B | 0.9000 | C23—H23A | 0.9700 |
C—C12 | 1.503 (3) | C23—H23B | 0.9700 |
C1—C2 | 1.383 (3) | C24—C25 | 1.511 (3) |
C1—H1A | 0.9300 | C24—H24A | 0.9700 |
C2—C3 | 1.384 (3) | C24—H24B | 0.9700 |
C2—H2A | 0.9300 | C25—H25A | 0.9700 |
C3—C4 | 1.388 (3) | C25—H25B | 0.9700 |
C3—H3A | 0.9300 | | |
| | | |
O2—Cu—O3 | 93.45 (6) | C10—C9—H9 | 120.7 |
O2—Cu—N2 | 92.17 (7) | N2—C10—C9 | 121.8 (2) |
O3—Cu—N2 | 171.98 (7) | N2—C10—H10 | 119.1 |
O2—Cu—N1 | 170.82 (6) | C9—C10—H10 | 119.1 |
O3—Cu—N1 | 92.60 (6) | O3—C11—C12 | 125.43 (18) |
N2—Cu—N1 | 81.16 (7) | O3—C11—C21 | 118.04 (18) |
O2—Cu—O4 | 89.69 (6) | C12—C11—C21 | 116.49 (18) |
O3—Cu—O4 | 89.45 (6) | C13—C12—C11 | 119.04 (18) |
N2—Cu—O4 | 96.31 (6) | C13—C12—C | 116.56 (18) |
N1—Cu—O4 | 97.27 (6) | C11—C12—C | 124.26 (18) |
C—O2—Cu | 126.64 (13) | N3—C13—C12 | 124.71 (19) |
C11—O3—Cu | 121.03 (13) | N3—C13—H13 | 117.6 |
N6—O4—Cu | 112.59 (13) | C12—C13—H13 | 117.6 |
H3—O10—H4 | 111 (2) | N3—C14—C15 | 114.55 (17) |
H1—O11—H2 | 108 (2) | N3—C14—H14A | 108.6 |
C1—N1—C5 | 119.11 (19) | C15—C14—H14A | 108.6 |
C1—N1—Cu | 126.54 (14) | N3—C14—H14B | 108.6 |
C5—N1—Cu | 114.21 (14) | C15—C14—H14B | 108.6 |
C10—N2—C6 | 119.68 (18) | H14A—C14—H14B | 107.6 |
C10—N2—Cu | 126.00 (15) | C14—C15—H15A | 109.5 |
C6—N2—Cu | 114.30 (14) | C14—C15—H15B | 109.5 |
C13—N3—C16 | 119.60 (18) | H15A—C15—H15B | 109.5 |
C13—N3—C14 | 121.63 (17) | C14—C15—H15C | 109.5 |
C16—N3—C14 | 118.77 (16) | H15A—C15—H15C | 109.5 |
C18—N4—C22 | 116.19 (17) | H15B—C15—H15C | 109.5 |
C18—N4—C25 | 114.54 (16) | N3—C16—C21 | 118.51 (17) |
C22—N4—C25 | 110.14 (16) | N3—C16—C17 | 121.03 (19) |
C24—N5—C23 | 111.55 (16) | C21—C16—C17 | 120.46 (19) |
C24—N5—H5A | 109.3 | C18—C17—C16 | 120.8 (2) |
C23—N5—H5A | 109.3 | C18—C17—H17 | 119.6 |
C24—N5—H5B | 109.3 | C16—C17—H17 | 119.6 |
C23—N5—H5B | 109.3 | C17—C18—N4 | 123.87 (19) |
H5A—N5—H5B | 108.0 | C17—C18—C19 | 116.98 (18) |
O6—N6—O5 | 120.4 (2) | N4—C18—C19 | 119.12 (18) |
O6—N6—O4 | 120.2 (2) | C20—C19—F | 118.54 (19) |
O5—N6—O4 | 119.4 (2) | C20—C19—C18 | 123.34 (19) |
O9—N7—O7 | 120.5 (2) | F—C19—C18 | 118.10 (17) |
O9—N7—O8 | 119.0 (2) | C19—C20—C21 | 119.9 (2) |
O7—N7—O8 | 120.5 (2) | C19—C20—H20 | 120.1 |
O1—C—O2 | 122.79 (18) | C21—C20—H20 | 120.1 |
O1—C—C12 | 117.48 (18) | C16—C21—C20 | 118.52 (18) |
O2—C—C12 | 119.70 (18) | C16—C21—C11 | 121.63 (19) |
N1—C1—C2 | 122.30 (19) | C20—C21—C11 | 119.85 (19) |
N1—C1—H1A | 118.8 | N4—C22—C23 | 110.50 (18) |
C2—C1—H1A | 118.8 | N4—C22—H22A | 109.6 |
C1—C2—C3 | 118.6 (2) | C23—C22—H22A | 109.6 |
C1—C2—H2A | 120.7 | N4—C22—H22B | 109.6 |
C3—C2—H2A | 120.7 | C23—C22—H22B | 109.6 |
C2—C3—C4 | 119.7 (2) | H22A—C22—H22B | 108.1 |
C2—C3—H3A | 120.2 | N5—C23—C22 | 111.52 (17) |
C4—C3—H3A | 120.2 | N5—C23—H23A | 109.3 |
C5—C4—C3 | 118.6 (2) | C22—C23—H23A | 109.3 |
C5—C4—H4A | 120.7 | N5—C23—H23B | 109.3 |
C3—C4—H4A | 120.7 | C22—C23—H23B | 109.3 |
N1—C5—C4 | 121.6 (2) | H23A—C23—H23B | 108.0 |
N1—C5—C6 | 114.14 (19) | N5—C24—C25 | 109.68 (17) |
C4—C5—C6 | 124.22 (19) | N5—C24—H24A | 109.7 |
N2—C6—C7 | 121.5 (2) | C25—C24—H24A | 109.7 |
N2—C6—C5 | 114.90 (17) | N5—C24—H24B | 109.7 |
C7—C6—C5 | 123.6 (2) | C25—C24—H24B | 109.7 |
C8—C7—C6 | 118.3 (2) | H24A—C24—H24B | 108.2 |
C8—C7—H7 | 120.9 | N4—C25—C24 | 110.20 (17) |
C6—C7—H7 | 120.9 | N4—C25—H25A | 109.6 |
C7—C8—C9 | 120.1 (2) | C24—C25—H25A | 109.6 |
C7—C8—H8 | 119.9 | N4—C25—H25B | 109.6 |
C9—C8—H8 | 119.9 | C24—C25—H25B | 109.6 |
C8—C9—C10 | 118.6 (2) | H25A—C25—H25B | 108.1 |
C8—C9—H9 | 120.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H3···O4 | 0.86 (2) | 2.02 (2) | 2.843 (3) | 161 (3) |
O10—H3···O6 | 0.86 (2) | 2.49 (2) | 3.167 (4) | 137 (3) |
O10—H3···N6 | 0.86 (2) | 2.57 (2) | 3.371 (3) | 157 (3) |
O10—H4···O9 | 0.85 (2) | 2.03 (2) | 2.829 (3) | 156 (3) |
O10—H4···O8 | 0.85 (2) | 2.65 (2) | 3.345 (3) | 140 (3) |
O10—H4···N7 | 0.85 (2) | 2.70 (2) | 3.517 (3) | 163 (3) |
O11—H1···O5i | 0.85 (2) | 1.99 (2) | 2.795 (3) | 157 (3) |
O11—H2···O8ii | 0.86 (2) | 2.08 (2) | 2.908 (3) | 164 (3) |
O11—H2···O7ii | 0.86 (2) | 2.40 (2) | 3.103 (3) | 139 (3) |
O11—H2···N7ii | 0.86 (2) | 2.57 (2) | 3.417 (3) | 168 (3) |
N5—H5A···O1iii | 0.90 | 1.79 | 2.686 (2) | 176 |
N5—H5B···O10i | 0.90 | 2.07 | 2.850 (3) | 144 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |