The crystal structure of the title compound, [CuCl(C12H8N2)2](C6H6NO3S)·3H2O, contains CuII cations five-coordinated by one chloride anion and four N atoms of two 1,10-phenanthroline ligands. Between the the 4-aminobenzenesulfonate anions and the uncoordinated water molecules intermolecular hydrogen bonding is found.
Supporting information
CCDC reference: 613782
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.037
- wR factor = 0.103
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O4
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.09
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C30 H26 Cl1 Cu1 N5 O6 S1
Atom count from _chemical_formula_moiety:C30 H28 Cl1 Cu1 N5 O6 S1
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 1.090
Tmax scaled 0.758 Tmin scaled 0.708
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.
Chlorobis(1,10-phenanthroline-
κ2N,
N')copper(II)
4-aminobenzenesulfonate trihydrate
top
Crystal data top
[CuCl(C12H8N2)2](C6H6NO3S)·3H2O | Z = 2 |
Mr = 683.61 | F(000) = 702 |
Triclinic, P1 | Dx = 1.537 Mg m−3 |
a = 8.1734 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.3367 (8) Å | Cell parameters from 2121 reflections |
c = 14.9091 (10) Å | θ = 2.2–27.2° |
α = 67.682 (1)° | µ = 0.95 mm−1 |
β = 84.243 (1)° | T = 293 K |
γ = 79.368 (1)° | Plate, green |
V = 1476.81 (16) Å3 | 0.35 × 0.33 × 0.29 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5178 independent reflections |
Radiation source: fine-focus sealed tube | 3770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −8→9 |
Tmin = 0.650, Tmax = 0.696 | k = −11→15 |
7595 measured reflections | l = −15→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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3 |
5178 reflections | (Δ/σ)max = 0.001 |
409 parameters | Δρmax = 0.34 e Å−3 |
15 restraints | Δρmin = −0.32 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 | Occ. (<1) |
Cu1 | 0.76030 (4) | 0.96783 (3) | 0.75822 (2) | 0.04419 (13) | |
Cl1 | 1.00910 (9) | 0.93488 (7) | 0.82929 (5) | 0.0587 (2) | |
N2 | 0.5366 (3) | 1.06256 (18) | 0.78544 (16) | 0.0448 (6) | |
N3 | 0.6707 (3) | 0.85383 (18) | 0.87281 (16) | 0.0447 (6) | |
N4 | 0.8271 (3) | 1.08498 (18) | 0.63819 (16) | 0.0434 (6) | |
N5 | 0.7066 (3) | 0.90686 (18) | 0.65389 (16) | 0.0425 (5) | |
C1 | 0.7441 (4) | 0.7509 (2) | 0.9153 (2) | 0.0563 (8) | |
H1 | 0.8428 | 0.7264 | 0.8878 | 0.068* | |
C2 | 0.6784 (5) | 0.6783 (3) | 0.9997 (2) | 0.0651 (9) | |
H2 | 0.7319 | 0.6062 | 1.0276 | 0.078* | |
C3 | 0.5352 (5) | 0.7141 (3) | 1.0404 (2) | 0.0662 (10) | |
H3 | 0.4905 | 0.6663 | 1.0969 | 0.079* | |
C4 | 0.4537 (4) | 0.8226 (3) | 0.9982 (2) | 0.0508 (8) | |
C5 | 0.3063 (4) | 0.8686 (3) | 1.0374 (2) | 0.0654 (10) | |
H5 | 0.2573 | 0.8249 | 1.0944 | 0.078* | |
C6 | 0.2359 (4) | 0.9747 (4) | 0.9934 (3) | 0.0677 (10) | |
H6 | 0.1401 | 1.0028 | 1.0208 | 0.081* | |
C7 | 0.3074 (4) | 1.0442 (3) | 0.9050 (2) | 0.0527 (8) | |
C8 | 0.2397 (4) | 1.1536 (3) | 0.8543 (3) | 0.0693 (10) | |
H8 | 0.1404 | 1.1850 | 0.8762 | 0.083* | |
C9 | 0.3203 (5) | 1.2137 (3) | 0.7729 (3) | 0.0719 (10) | |
H9 | 0.2753 | 1.2863 | 0.7386 | 0.086* | |
C10 | 0.4701 (4) | 1.1672 (2) | 0.7403 (2) | 0.0579 (8) | |
H10 | 0.5250 | 1.2105 | 0.6856 | 0.070* | |
C11 | 0.4544 (3) | 1.0024 (2) | 0.86657 (19) | 0.0423 (7) | |
C12 | 0.5285 (3) | 0.8900 (2) | 0.91313 (18) | 0.0419 (7) | |
C13 | 0.6470 (4) | 0.8171 (2) | 0.6633 (2) | 0.0553 (8) | |
H13 | 0.6232 | 0.7691 | 0.7255 | 0.066* | |
C14 | 0.6184 (4) | 0.7914 (3) | 0.5845 (3) | 0.0618 (9) | |
H14 | 0.5757 | 0.7280 | 0.5941 | 0.074* | |
C15 | 0.6537 (4) | 0.8602 (3) | 0.4936 (3) | 0.0610 (9) | |
H15 | 0.6374 | 0.8432 | 0.4405 | 0.073* | |
C16 | 0.7149 (3) | 0.9571 (2) | 0.4792 (2) | 0.0466 (7) | |
C17 | 0.7559 (4) | 1.0342 (3) | 0.3872 (2) | 0.0581 (8) | |
H17 | 0.7401 | 1.0222 | 0.3314 | 0.070* | |
C18 | 0.8173 (4) | 1.1242 (3) | 0.3791 (2) | 0.0604 (9) | |
H18 | 0.8429 | 1.1731 | 0.3177 | 0.073* | |
C19 | 0.8442 (3) | 1.1468 (2) | 0.4623 (2) | 0.0470 (7) | |
C20 | 0.9116 (4) | 1.2374 (2) | 0.4600 (2) | 0.0590 (9) | |
H20 | 0.9397 | 1.2895 | 0.4009 | 0.071* | |
C21 | 0.9354 (4) | 1.2488 (2) | 0.5436 (3) | 0.0616 (9) | |
H21 | 0.9807 | 1.3086 | 0.5419 | 0.074* | |
C22 | 0.8928 (4) | 1.1714 (2) | 0.6330 (2) | 0.0567 (8) | |
H22 | 0.9106 | 1.1805 | 0.6899 | 0.068* | |
C23 | 0.8039 (3) | 1.0720 (2) | 0.55480 (19) | 0.0397 (6) | |
C24 | 0.7398 (3) | 0.9758 (2) | 0.56252 (19) | 0.0393 (6) | |
S1 | 0.11579 (9) | 0.56459 (7) | 0.25897 (5) | 0.0513 (2) | |
O1 | 0.0607 (4) | 0.5000 (3) | 0.35310 (19) | 0.0876 (11) | 0.83 |
O2 | 0.0197 (3) | 0.5674 (3) | 0.1819 (2) | 0.0755 (9) | 0.83 |
O3 | 0.1201 (4) | 0.6771 (2) | 0.2506 (3) | 0.0928 (11) | 0.83 |
O1' | 0.0387 (16) | 0.4640 (10) | 0.2779 (11) | 0.072 (4)* | 0.17 |
O2' | 0.1043 (16) | 0.5851 (11) | 0.3465 (8) | 0.060 (3)* | 0.17 |
O3' | 0.0723 (17) | 0.6525 (10) | 0.1757 (8) | 0.065 (3)* | 0.17 |
N1 | 0.8207 (3) | 0.3944 (2) | 0.18581 (19) | 0.0616 (7) | |
H1N1 | 0.8353 | 0.3835 | 0.1321 | 0.092* | |
H2N1 | 0.8923 | 0.4275 | 0.1973 | 0.092* | |
C25 | 0.6568 (4) | 0.4313 (2) | 0.2039 (2) | 0.0447 (7) | |
C26 | 0.6151 (4) | 0.4808 (2) | 0.2719 (2) | 0.0485 (7) | |
H26 | 0.6988 | 0.4881 | 0.3058 | 0.058* | |
C27 | 0.4504 (4) | 0.5194 (2) | 0.2899 (2) | 0.0455 (7) | |
H27 | 0.4246 | 0.5523 | 0.3356 | 0.055* | |
C28 | 0.3242 (3) | 0.5092 (2) | 0.23981 (18) | 0.0397 (6) | |
C29 | 0.3642 (4) | 0.4591 (2) | 0.1729 (2) | 0.0439 (7) | |
H29 | 0.2800 | 0.4511 | 0.1397 | 0.053* | |
C30 | 0.5272 (4) | 0.4208 (2) | 0.1551 (2) | 0.0481 (7) | |
H30 | 0.5518 | 0.3873 | 0.1098 | 0.058* | |
O4 | 0.5364 (4) | 0.3511 (2) | 0.5332 (2) | 0.1019 (9) | |
O5 | 0.2207 (3) | 0.4668 (2) | 0.52941 (18) | 0.0965 (9) | |
H1O5 | 0.1408 | 0.4718 | 0.5663 | 0.145* | |
H2O5 | 0.1932 | 0.4862 | 0.4732 | 0.145* | |
O6 | 0.1333 (3) | 0.6787 (2) | 0.98344 (17) | 0.0861 (8) | |
H1O6 | 0.0866 | 0.6591 | 1.0372 | 0.129* | |
H2O6 | 0.0945 | 0.7404 | 0.9468 | 0.129* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0521 (2) | 0.0414 (2) | 0.0359 (2) | −0.01438 (16) | 0.00316 (15) | −0.00876 (15) |
Cl1 | 0.0545 (5) | 0.0843 (6) | 0.0399 (4) | −0.0212 (4) | 0.0013 (3) | −0.0218 (4) |
N2 | 0.0562 (15) | 0.0414 (13) | 0.0366 (13) | −0.0098 (12) | −0.0039 (11) | −0.0125 (11) |
N3 | 0.0476 (14) | 0.0419 (13) | 0.0391 (13) | −0.0120 (11) | −0.0002 (11) | −0.0071 (10) |
N4 | 0.0500 (14) | 0.0404 (13) | 0.0408 (13) | −0.0116 (11) | 0.0031 (11) | −0.0153 (10) |
N5 | 0.0491 (14) | 0.0382 (13) | 0.0397 (13) | −0.0128 (11) | −0.0001 (10) | −0.0116 (10) |
C1 | 0.059 (2) | 0.0436 (18) | 0.0573 (19) | −0.0136 (15) | −0.0050 (16) | −0.0056 (15) |
C2 | 0.082 (3) | 0.0495 (19) | 0.052 (2) | −0.0173 (18) | −0.0135 (18) | 0.0006 (16) |
C3 | 0.088 (3) | 0.065 (2) | 0.0418 (18) | −0.042 (2) | −0.0048 (18) | −0.0018 (16) |
C4 | 0.0550 (18) | 0.069 (2) | 0.0352 (16) | −0.0319 (16) | −0.0004 (14) | −0.0168 (15) |
C5 | 0.068 (2) | 0.101 (3) | 0.0429 (19) | −0.046 (2) | 0.0109 (17) | −0.032 (2) |
C6 | 0.050 (2) | 0.117 (3) | 0.065 (2) | −0.033 (2) | 0.0137 (17) | −0.059 (2) |
C7 | 0.0454 (17) | 0.073 (2) | 0.0577 (19) | −0.0135 (16) | −0.0031 (15) | −0.0420 (17) |
C8 | 0.050 (2) | 0.084 (3) | 0.095 (3) | −0.0001 (19) | −0.008 (2) | −0.059 (2) |
C9 | 0.072 (2) | 0.055 (2) | 0.092 (3) | 0.0138 (19) | −0.026 (2) | −0.036 (2) |
C10 | 0.069 (2) | 0.0459 (18) | 0.058 (2) | −0.0044 (17) | −0.0145 (17) | −0.0174 (15) |
C11 | 0.0400 (15) | 0.0552 (18) | 0.0420 (16) | −0.0126 (13) | −0.0044 (13) | −0.0263 (14) |
C12 | 0.0476 (17) | 0.0495 (17) | 0.0329 (14) | −0.0196 (14) | −0.0013 (13) | −0.0147 (13) |
C13 | 0.066 (2) | 0.0443 (17) | 0.0558 (19) | −0.0191 (15) | −0.0009 (16) | −0.0137 (15) |
C14 | 0.067 (2) | 0.0495 (19) | 0.080 (3) | −0.0150 (17) | −0.0075 (19) | −0.0329 (18) |
C15 | 0.056 (2) | 0.072 (2) | 0.069 (2) | −0.0026 (17) | −0.0117 (17) | −0.0419 (19) |
C16 | 0.0411 (16) | 0.0553 (18) | 0.0445 (17) | 0.0028 (14) | −0.0051 (13) | −0.0236 (14) |
C17 | 0.059 (2) | 0.077 (2) | 0.0395 (17) | −0.0059 (18) | 0.0012 (15) | −0.0259 (16) |
C18 | 0.057 (2) | 0.072 (2) | 0.0340 (17) | 0.0016 (18) | 0.0069 (14) | −0.0070 (15) |
C19 | 0.0407 (16) | 0.0421 (16) | 0.0446 (17) | 0.0010 (13) | 0.0078 (13) | −0.0065 (13) |
C20 | 0.055 (2) | 0.0405 (17) | 0.061 (2) | −0.0089 (15) | 0.0156 (16) | 0.0003 (15) |
C21 | 0.067 (2) | 0.0361 (17) | 0.076 (2) | −0.0196 (15) | 0.0148 (19) | −0.0143 (16) |
C22 | 0.065 (2) | 0.0479 (18) | 0.062 (2) | −0.0175 (16) | 0.0069 (16) | −0.0239 (16) |
C23 | 0.0358 (14) | 0.0393 (15) | 0.0385 (15) | −0.0034 (12) | 0.0034 (12) | −0.0104 (12) |
C24 | 0.0347 (14) | 0.0384 (15) | 0.0405 (15) | −0.0034 (12) | 0.0018 (12) | −0.0118 (12) |
S1 | 0.0476 (4) | 0.0639 (5) | 0.0445 (4) | −0.0124 (4) | 0.0066 (3) | −0.0227 (4) |
O1 | 0.0675 (19) | 0.115 (3) | 0.0478 (17) | −0.0070 (18) | 0.0250 (15) | −0.0039 (17) |
O2 | 0.0497 (16) | 0.122 (3) | 0.0620 (18) | −0.0123 (17) | −0.0030 (14) | −0.0421 (18) |
O3 | 0.071 (2) | 0.064 (2) | 0.157 (3) | −0.0016 (16) | 0.001 (2) | −0.062 (2) |
N1 | 0.0544 (16) | 0.0597 (17) | 0.0685 (18) | −0.0027 (13) | 0.0039 (14) | −0.0257 (14) |
C25 | 0.0517 (18) | 0.0341 (15) | 0.0413 (16) | −0.0109 (13) | 0.0037 (14) | −0.0057 (12) |
C26 | 0.0509 (18) | 0.0485 (17) | 0.0441 (16) | −0.0117 (14) | −0.0023 (14) | −0.0129 (14) |
C27 | 0.0582 (19) | 0.0444 (16) | 0.0350 (15) | −0.0147 (14) | 0.0053 (13) | −0.0145 (12) |
C28 | 0.0487 (16) | 0.0352 (14) | 0.0358 (15) | −0.0173 (13) | 0.0044 (12) | −0.0105 (12) |
C29 | 0.0499 (17) | 0.0445 (16) | 0.0430 (16) | −0.0172 (14) | 0.0023 (13) | −0.0190 (13) |
C30 | 0.064 (2) | 0.0405 (16) | 0.0467 (17) | −0.0173 (15) | 0.0093 (15) | −0.0229 (13) |
O4 | 0.111 (2) | 0.094 (2) | 0.087 (2) | −0.0068 (17) | −0.0092 (17) | −0.0215 (16) |
O5 | 0.0644 (16) | 0.142 (3) | 0.0701 (17) | −0.0028 (16) | 0.0069 (13) | −0.0331 (17) |
O6 | 0.0956 (19) | 0.0935 (19) | 0.0601 (15) | 0.0024 (15) | −0.0060 (14) | −0.0254 (14) |
Geometric parameters (Å, º) top
Cu1—N4 | 1.984 (2) | C16—C24 | 1.397 (4) |
Cu1—N3 | 1.989 (2) | C16—C17 | 1.420 (4) |
Cu1—N2 | 2.119 (2) | C17—C18 | 1.345 (4) |
Cu1—N5 | 2.122 (2) | C17—H17 | 0.9300 |
Cu1—Cl1 | 2.2804 (9) | C18—C19 | 1.429 (4) |
N2—C10 | 1.333 (4) | C18—H18 | 0.9300 |
N2—C11 | 1.363 (3) | C19—C20 | 1.405 (4) |
N3—C1 | 1.325 (3) | C19—C23 | 1.411 (4) |
N3—C12 | 1.348 (3) | C20—C21 | 1.349 (5) |
N4—C22 | 1.332 (4) | C20—H20 | 0.9300 |
N4—C23 | 1.354 (3) | C21—C22 | 1.399 (4) |
N5—C13 | 1.328 (4) | C21—H21 | 0.9300 |
N5—C24 | 1.357 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.393 (4) | C23—C24 | 1.434 (4) |
C1—H1 | 0.9300 | S1—O3' | 1.368 (10) |
C2—C3 | 1.356 (5) | S1—O1 | 1.419 (3) |
C2—H2 | 0.9300 | S1—O2' | 1.423 (10) |
C3—C4 | 1.404 (5) | S1—O2 | 1.441 (3) |
C3—H3 | 0.9300 | S1—O3 | 1.465 (3) |
C4—C12 | 1.404 (4) | S1—O1' | 1.505 (11) |
C4—C5 | 1.424 (5) | S1—C28 | 1.769 (3) |
C5—C6 | 1.354 (5) | N1—C25 | 1.376 (4) |
C5—H5 | 0.9300 | N1—H1N1 | 0.8600 |
C6—C7 | 1.433 (5) | N1—H2N1 | 0.8601 |
C6—H6 | 0.9300 | C25—C26 | 1.392 (4) |
C7—C11 | 1.394 (4) | C25—C30 | 1.399 (4) |
C7—C8 | 1.398 (5) | C26—C27 | 1.388 (4) |
C8—C9 | 1.358 (5) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.386 (4) |
C9—C10 | 1.396 (5) | C27—H27 | 0.9300 |
C9—H9 | 0.9300 | C28—C29 | 1.381 (4) |
C10—H10 | 0.9300 | C29—C30 | 1.374 (4) |
C11—C12 | 1.433 (4) | C29—H29 | 0.9300 |
C13—C14 | 1.394 (4) | C30—H30 | 0.9300 |
C13—H13 | 0.9300 | O5—H1O5 | 0.8200 |
C14—C15 | 1.355 (5) | O5—H2O5 | 0.8200 |
C14—H14 | 0.9300 | O6—H1O6 | 0.8201 |
C15—C16 | 1.404 (4) | O6—H2O6 | 0.8201 |
C15—H15 | 0.9300 | | |
| | | |
N4—Cu1—N3 | 174.18 (10) | C15—C16—C17 | 124.6 (3) |
N4—Cu1—N2 | 95.70 (9) | C18—C17—C16 | 121.3 (3) |
N3—Cu1—N2 | 80.49 (9) | C18—C17—H17 | 119.4 |
N4—Cu1—N5 | 80.59 (9) | C16—C17—H17 | 119.4 |
N3—Cu1—N5 | 96.22 (9) | C17—C18—C19 | 121.8 (3) |
N2—Cu1—N5 | 106.64 (9) | C17—C18—H18 | 119.1 |
N4—Cu1—Cl1 | 93.93 (7) | C19—C18—H18 | 119.1 |
N3—Cu1—Cl1 | 91.87 (7) | C20—C19—C23 | 116.5 (3) |
N2—Cu1—Cl1 | 126.75 (7) | C20—C19—C18 | 125.1 (3) |
N5—Cu1—Cl1 | 126.60 (7) | C23—C19—C18 | 118.3 (3) |
C10—N2—C11 | 117.4 (3) | C21—C20—C19 | 119.9 (3) |
C10—N2—Cu1 | 131.7 (2) | C21—C20—H20 | 120.0 |
C11—N2—Cu1 | 110.82 (18) | C19—C20—H20 | 120.0 |
C1—N3—C12 | 119.0 (2) | C20—C21—C22 | 120.6 (3) |
C1—N3—Cu1 | 125.9 (2) | C20—C21—H21 | 119.7 |
C12—N3—Cu1 | 114.87 (18) | C22—C21—H21 | 119.7 |
C22—N4—C23 | 118.7 (2) | N4—C22—C21 | 121.3 (3) |
C22—N4—Cu1 | 126.6 (2) | N4—C22—H22 | 119.3 |
C23—N4—Cu1 | 114.75 (18) | C21—C22—H22 | 119.3 |
C13—N5—C24 | 117.4 (2) | N4—C23—C19 | 122.9 (3) |
C13—N5—Cu1 | 131.6 (2) | N4—C23—C24 | 117.6 (2) |
C24—N5—Cu1 | 110.98 (17) | C19—C23—C24 | 119.4 (3) |
N3—C1—C2 | 122.3 (3) | N5—C24—C16 | 123.6 (3) |
N3—C1—H1 | 118.9 | N5—C24—C23 | 116.0 (2) |
C2—C1—H1 | 118.9 | C16—C24—C23 | 120.4 (2) |
C3—C2—C1 | 119.0 (3) | O3'—S1—O1 | 145.4 (6) |
C3—C2—H2 | 120.5 | O3'—S1—O2' | 117.1 (8) |
C1—C2—H2 | 120.5 | O1—S1—O2' | 50.8 (5) |
C2—C3—C4 | 120.6 (3) | O3'—S1—O2 | 53.0 (6) |
C2—C3—H3 | 119.7 | O1—S1—O2 | 114.0 (2) |
C4—C3—H3 | 119.7 | O2'—S1—O2 | 143.6 (5) |
C3—C4—C12 | 116.5 (3) | O3'—S1—O3 | 58.5 (6) |
C3—C4—C5 | 124.6 (3) | O1—S1—O3 | 111.5 (2) |
C12—C4—C5 | 118.8 (3) | O2'—S1—O3 | 62.6 (6) |
C6—C5—C4 | 121.4 (3) | O2—S1—O3 | 109.3 (2) |
C6—C5—H5 | 119.3 | O3'—S1—O1' | 116.6 (9) |
C4—C5—H5 | 119.3 | O1—S1—O1' | 57.8 (6) |
C5—C6—C7 | 120.8 (3) | O2'—S1—O1' | 108.2 (8) |
C5—C6—H6 | 119.6 | O2—S1—O1' | 64.0 (6) |
C7—C6—H6 | 119.6 | O3—S1—O1' | 156.5 (5) |
C11—C7—C8 | 116.9 (3) | O3'—S1—C28 | 106.3 (6) |
C11—C7—C6 | 119.0 (3) | O1—S1—C28 | 108.31 (15) |
C8—C7—C6 | 124.0 (3) | O2'—S1—C28 | 108.7 (5) |
C9—C8—C7 | 119.4 (3) | O2—S1—C28 | 107.68 (14) |
C9—C8—H8 | 120.3 | O3—S1—C28 | 105.58 (15) |
C7—C8—H8 | 120.3 | O1'—S1—C28 | 97.9 (5) |
C8—C9—C10 | 120.5 (3) | C25—N1—H1N1 | 112.5 |
C8—C9—H9 | 119.8 | C25—N1—H2N1 | 115.3 |
C10—C9—H9 | 119.8 | H1N1—N1—H2N1 | 116.2 |
N2—C10—C9 | 121.8 (3) | N1—C25—C26 | 120.5 (3) |
N2—C10—H10 | 119.1 | N1—C25—C30 | 121.7 (3) |
C9—C10—H10 | 119.1 | C26—C25—C30 | 117.8 (3) |
N2—C11—C7 | 123.9 (3) | C27—C26—C25 | 121.0 (3) |
N2—C11—C12 | 116.1 (2) | C27—C26—H26 | 119.5 |
C7—C11—C12 | 120.0 (3) | C25—C26—H26 | 119.5 |
N3—C12—C4 | 122.6 (3) | C28—C27—C26 | 120.2 (3) |
N3—C12—C11 | 117.6 (2) | C28—C27—H27 | 119.9 |
C4—C12—C11 | 119.9 (3) | C26—C27—H27 | 119.9 |
N5—C13—C14 | 123.1 (3) | C29—C28—C27 | 119.3 (3) |
N5—C13—H13 | 118.5 | C29—C28—S1 | 120.9 (2) |
C14—C13—H13 | 118.5 | C27—C28—S1 | 119.8 (2) |
C15—C14—C13 | 119.1 (3) | C30—C29—C28 | 120.6 (3) |
C15—C14—H14 | 120.5 | C30—C29—H29 | 119.7 |
C13—C14—H14 | 120.5 | C28—C29—H29 | 119.7 |
C14—C15—C16 | 120.3 (3) | C29—C30—C25 | 121.2 (3) |
C14—C15—H15 | 119.9 | C29—C30—H30 | 119.4 |
C16—C15—H15 | 119.9 | C25—C30—H30 | 119.4 |
C24—C16—C15 | 116.6 (3) | H1O5—O5—H2O5 | 112.3 |
C24—C16—C17 | 118.8 (3) | H1O6—O6—H2O6 | 114.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O6i | 0.86 | 2.15 | 3.000 (4) | 168 |
N1—H2N1···O1′ii | 0.86 | 2.01 | 2.826 (13) | 157 |
N1—H2N1···O2ii | 0.86 | 2.23 | 3.040 (4) | 157 |
O5—H1O5···O1iii | 0.82 | 2.00 | 2.822 (3) | 174 |
O5—H1O5···O2′iii | 0.82 | 2.36 | 3.111 (13) | 153 |
O5—H2O5···O2′ | 0.82 | 1.97 | 2.744 (12) | 158 |
O5—H2O5···O1 | 0.82 | 2.12 | 2.900 (4) | 160 |
O6—H1O6···O3′iv | 0.82 | 2.03 | 2.757 (13) | 148 |
O6—H1O6···O2iv | 0.82 | 2.11 | 2.905 (4) | 163 |
O6—H2O6···Cl1v | 0.82 | 2.53 | 3.348 (3) | 173 |
N1—H2N1···O1′ii | 0.86 | 2.01 | 2.826 (13) | 157 |
N1—H1N1···O6i | 0.86 | 2.15 | 3.000 (4) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x, y, z+1; (v) x−1, y, z. |