In the molecule of the title compound, [Pt(C14H12N2)(C2H4D4N2)]Cl2·3D2O, the complex dication has square-planar coordination to the PtII atom from N-donor atoms. A small tilt of 4.34 (6)° is observed between the plane of the phenanthroline (phen) ligand and the coordination plane. The phen ligands are assembled along [010], with π–π stacking interactions between phen ligands of interleaved complexes. The structure also reveals hydrogen-bond interactions between the complex ion, its counter-ions and the solvent molecules. The introduction of methyl residues onto the phen ligand at positions 4 and 7 does not appear to alter the geometry of the complex significantly.
Supporting information
CCDC reference: 627791
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.018
- wR factor = 0.038
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B
CHEMS01_ALERT_1_B The sum formula contains elements in the wrong order.
D precedes Cl
Sequence must be C, H, then alphabetical.
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.54
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
PLAT731_ALERT_1_C Bond Calc 0.87(4), Rep 0.864(18) ...... 2.22 su-Ra
O1 -D1OA 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.87(4), Rep 0.864(18) ...... 2.22 su-Ra
O1 -D1# 1.555 1.555
Alert level G
CHEMS02_ALERT_1_G Please check that you have entered the correct
_publ_requested_category classification of your compound;
FI or CI or EI for inorganic; FM or CM or EM for metal-organic;
FO or CO or EO for organic.
From the CIF: _publ_requested_category FI
From the CIF: _chemical_formula_sum:C16 H16 Cl2 D10 N4 O3 Pt1
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal3.6 (Hall et al., 1999), ORTEPII (Johnson, 1976) and
WinGX (Farrugia, 1999); software used to prepare material for publication: Please provide details.
(4,7-Dimethyl-1,10-phenanthroline)(ethylenediamine)platinum(II) dichloride
tris(deuterium oxide) solvate
top
Crystal data top
[Pt(C14H12N2)(C2H4D4N2)]Cl2·3D2O | F(000) = 1144 |
Mr = 598.41 | Dx = 2.022 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 998 reflections |
a = 11.3986 (16) Å | θ = 3.4–28.2° |
b = 7.1092 (10) Å | µ = 7.44 mm−1 |
c = 24.761 (4) Å | T = 150 K |
β = 101.623 (2)° | Acicular, pale yellow |
V = 1965.4 (5) Å3 | 0.44 × 0.06 × 0.05 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 4717 independent reflections |
Radiation source: sealed tube | 4126 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: gaussian [GAUSSIAN (Coppens et al., 1965) and XPREP (Siemens,
1995)] | h = −15→14 |
Tmin = 0.212, Tmax = 0.720 | k = −9→9 |
19380 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)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
4717 reflections | (Δ/σ)max = 0.007 |
277 parameters | Δρmax = 1.63 e Å−3 |
6 restraints | Δρmin = −0.46 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 | |
Pt1 | 0.165236 (8) | 0.283357 (14) | 0.134989 (4) | 0.01609 (3) | |
Cl1 | 0.50565 (6) | 1.01946 (9) | 0.13521 (3) | 0.02524 (14) | |
Cl2 | 0.09978 (6) | 0.83682 (10) | 0.23482 (3) | 0.02766 (15) | |
O1 | 0.3207 (2) | 0.7443 (3) | 0.17359 (10) | 0.0334 (5) | |
D1OA | 0.264 (3) | 0.790 (5) | 0.1885 (16) | 0.066 (13)* | |
D1OB | 0.368 (3) | 0.836 (4) | 0.1691 (13) | 0.045 (10)* | |
O2 | 0.51405 (19) | 0.5763 (3) | 0.09879 (9) | 0.0317 (5) | |
D2OA | 0.510 (3) | 0.697 (3) | 0.1065 (15) | 0.053 (11)* | |
D2OB | 0.561 (3) | 0.529 (5) | 0.1268 (11) | 0.066 (13)* | |
O3 | 0.63999 (19) | 0.3840 (3) | 0.19053 (9) | 0.0338 (5) | |
D3OA | 0.613 (3) | 0.273 (3) | 0.1812 (12) | 0.025 (8)* | |
D3OB | 0.710 (2) | 0.363 (5) | 0.2103 (12) | 0.053 (11)* | |
N1 | 0.33826 (19) | 0.3469 (4) | 0.16913 (9) | 0.0194 (4) | |
D1NA | 0.388 (3) | 0.285 (4) | 0.1552 (13) | 0.032 (9)* | |
D1NB | 0.346 (3) | 0.474 (5) | 0.1626 (12) | 0.040 (9)* | |
N2 | 0.1488 (2) | 0.2748 (3) | 0.21565 (9) | 0.0207 (5) | |
D2NA | 0.143 (2) | 0.147 (4) | 0.2273 (11) | 0.030 (8)* | |
D2NB | 0.089 (3) | 0.331 (4) | 0.2206 (13) | 0.033 (9)* | |
N3 | −0.00611 (19) | 0.2224 (3) | 0.09975 (9) | 0.0185 (4) | |
N4 | 0.17890 (19) | 0.2942 (3) | 0.05470 (9) | 0.0187 (4) | |
C1 | 0.3637 (2) | 0.2989 (4) | 0.22920 (11) | 0.0254 (6) | |
H1A | 0.4361 | 0.3662 | 0.2485 | 0.030* | |
H1B | 0.3776 | 0.1620 | 0.2343 | 0.030* | |
C2 | 0.2564 (2) | 0.3578 (4) | 0.25192 (10) | 0.0234 (6) | |
H2A | 0.2637 | 0.3116 | 0.2902 | 0.028* | |
H2B | 0.2500 | 0.4967 | 0.2522 | 0.028* | |
C3 | −0.0970 (2) | 0.1828 (3) | 0.12430 (11) | 0.0215 (6) | |
H3 | −0.0824 | 0.1727 | 0.1633 | 0.026* | |
C4 | −0.2130 (2) | 0.1559 (4) | 0.09420 (11) | 0.0230 (6) | |
H4 | −0.2753 | 0.1279 | 0.1133 | 0.028* | |
C5 | −0.2399 (2) | 0.1686 (3) | 0.03758 (11) | 0.0201 (5) | |
C6 | −0.1425 (2) | 0.2031 (3) | 0.01076 (11) | 0.0191 (5) | |
C7 | −0.1544 (2) | 0.2145 (4) | −0.04820 (11) | 0.0226 (5) | |
H7 | −0.2310 | 0.1974 | −0.0713 | 0.027* | |
C8 | −0.0587 (3) | 0.2491 (3) | −0.07146 (11) | 0.0222 (6) | |
H8 | −0.0696 | 0.2542 | −0.1105 | 0.027* | |
C9 | 0.0589 (2) | 0.2783 (3) | −0.03854 (10) | 0.0185 (5) | |
C10 | 0.1630 (2) | 0.3159 (3) | −0.06028 (11) | 0.0210 (6) | |
C11 | 0.2694 (2) | 0.3410 (4) | −0.02327 (11) | 0.0231 (6) | |
H11 | 0.3403 | 0.3659 | −0.0367 | 0.028* | |
C12 | 0.2755 (2) | 0.3307 (4) | 0.03368 (11) | 0.0219 (6) | |
H12 | 0.3503 | 0.3501 | 0.0580 | 0.026* | |
C13 | 0.0720 (2) | 0.2678 (3) | 0.01880 (10) | 0.0172 (5) | |
C14 | −0.0288 (2) | 0.2301 (3) | 0.04330 (10) | 0.0163 (5) | |
C15 | −0.3659 (2) | 0.1499 (4) | 0.00638 (11) | 0.0278 (6) | |
H15A | −0.4172 | 0.1088 | 0.0315 | 0.042* | |
H15B | −0.3691 | 0.0570 | −0.0231 | 0.042* | |
H15C | −0.3940 | 0.2718 | −0.0097 | 0.042* | |
C16 | 0.1564 (3) | 0.3297 (4) | −0.12116 (11) | 0.0295 (7) | |
H16A | 0.2342 | 0.3698 | −0.1282 | 0.044* | |
H16B | 0.0951 | 0.4217 | −0.1370 | 0.044* | |
H16C | 0.1356 | 0.2065 | −0.1382 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pt1 | 0.01361 (5) | 0.02056 (5) | 0.01443 (5) | −0.00102 (4) | 0.00359 (4) | −0.00121 (4) |
Cl1 | 0.0238 (3) | 0.0265 (3) | 0.0265 (3) | −0.0024 (3) | 0.0077 (3) | 0.0002 (3) |
Cl2 | 0.0206 (3) | 0.0358 (4) | 0.0273 (4) | −0.0011 (3) | 0.0065 (3) | 0.0042 (3) |
O1 | 0.0347 (13) | 0.0304 (12) | 0.0397 (13) | −0.0050 (9) | 0.0188 (10) | −0.0023 (9) |
O2 | 0.0319 (12) | 0.0308 (12) | 0.0312 (12) | 0.0015 (10) | 0.0034 (9) | 0.0021 (10) |
O3 | 0.0316 (13) | 0.0282 (13) | 0.0366 (13) | 0.0002 (10) | −0.0049 (10) | −0.0006 (9) |
N1 | 0.0144 (11) | 0.0260 (12) | 0.0178 (11) | −0.0023 (9) | 0.0033 (9) | −0.0004 (10) |
N2 | 0.0153 (12) | 0.0283 (12) | 0.0191 (11) | −0.0004 (10) | 0.0050 (9) | −0.0015 (10) |
N3 | 0.0156 (11) | 0.0228 (10) | 0.0177 (11) | −0.0019 (9) | 0.0051 (8) | −0.0017 (9) |
N4 | 0.0198 (11) | 0.0192 (11) | 0.0185 (11) | −0.0012 (9) | 0.0069 (9) | −0.0018 (9) |
C1 | 0.0205 (14) | 0.0360 (16) | 0.0188 (13) | −0.0013 (11) | 0.0015 (11) | 0.0013 (11) |
C2 | 0.0226 (14) | 0.0328 (14) | 0.0148 (13) | −0.0029 (12) | 0.0036 (10) | −0.0012 (11) |
C3 | 0.0213 (14) | 0.0241 (15) | 0.0205 (13) | −0.0033 (10) | 0.0076 (11) | −0.0023 (10) |
C4 | 0.0183 (13) | 0.0257 (13) | 0.0261 (14) | −0.0048 (11) | 0.0068 (11) | −0.0010 (11) |
C5 | 0.0186 (13) | 0.0181 (13) | 0.0231 (13) | −0.0031 (10) | 0.0034 (11) | −0.0013 (10) |
C6 | 0.0210 (13) | 0.0149 (12) | 0.0215 (13) | 0.0002 (10) | 0.0042 (10) | −0.0006 (10) |
C7 | 0.0213 (14) | 0.0234 (13) | 0.0208 (13) | −0.0016 (11) | −0.0012 (11) | −0.0006 (11) |
C8 | 0.0283 (15) | 0.0196 (14) | 0.0176 (13) | 0.0002 (10) | 0.0023 (11) | 0.0004 (10) |
C9 | 0.0236 (13) | 0.0155 (11) | 0.0168 (12) | 0.0005 (10) | 0.0053 (10) | −0.0002 (10) |
C10 | 0.0299 (15) | 0.0161 (14) | 0.0193 (13) | 0.0011 (10) | 0.0105 (11) | 0.0010 (10) |
C11 | 0.0225 (14) | 0.0250 (14) | 0.0248 (14) | −0.0022 (11) | 0.0121 (11) | −0.0008 (11) |
C12 | 0.0169 (13) | 0.0252 (14) | 0.0253 (14) | −0.0006 (10) | 0.0079 (11) | −0.0002 (11) |
C13 | 0.0177 (13) | 0.0144 (12) | 0.0196 (13) | 0.0015 (9) | 0.0042 (10) | 0.0003 (9) |
C14 | 0.0188 (13) | 0.0124 (11) | 0.0181 (12) | 0.0000 (9) | 0.0048 (10) | −0.0005 (9) |
C15 | 0.0182 (14) | 0.0362 (15) | 0.0282 (15) | −0.0041 (12) | 0.0025 (11) | 0.0011 (12) |
C16 | 0.0358 (18) | 0.0355 (17) | 0.0188 (14) | −0.0067 (12) | 0.0096 (12) | 0.0003 (11) |
Geometric parameters (Å, º) top
Pt1—N3 | 2.019 (2) | C3—H3 | 0.9500 |
Pt1—N4 | 2.027 (2) | C4—C5 | 1.376 (4) |
Pt1—N1 | 2.034 (2) | C4—H4 | 0.9500 |
Pt1—N2 | 2.044 (2) | C5—C6 | 1.425 (3) |
O1—D1OA | 0.864 (18) | C5—C15 | 1.493 (3) |
O1—D1OB | 0.868 (18) | C6—C14 | 1.395 (3) |
O2—D2OA | 0.881 (18) | C6—C7 | 1.441 (4) |
O2—D2OB | 0.856 (18) | C7—C8 | 1.355 (4) |
O3—D3OA | 0.857 (17) | C7—H7 | 0.9500 |
O3—D3OB | 0.861 (18) | C8—C9 | 1.436 (4) |
N1—C1 | 1.497 (3) | C8—H8 | 0.9500 |
N1—D1NA | 0.84 (3) | C9—C13 | 1.400 (3) |
N1—D1NB | 0.93 (3) | C9—C10 | 1.424 (4) |
N2—C2 | 1.488 (3) | C10—C11 | 1.376 (4) |
N2—D2NA | 0.96 (3) | C10—C16 | 1.497 (3) |
N2—D2NB | 0.82 (3) | C11—C12 | 1.400 (4) |
N3—C3 | 1.332 (3) | C11—H11 | 0.9500 |
N3—C14 | 1.370 (3) | C12—H12 | 0.9500 |
N4—C12 | 1.334 (3) | C13—C14 | 1.429 (3) |
N4—C13 | 1.368 (3) | C15—H15A | 0.9800 |
C1—C2 | 1.505 (4) | C15—H15B | 0.9800 |
C1—H1A | 0.9900 | C15—H15C | 0.9800 |
C1—H1B | 0.9900 | C16—H16A | 0.9800 |
C2—H2A | 0.9900 | C16—H16B | 0.9800 |
C2—H2B | 0.9900 | C16—H16C | 0.9800 |
C3—C4 | 1.394 (4) | | |
| | | |
N3—Pt1—N4 | 80.97 (8) | C3—C4—H4 | 119.1 |
N3—Pt1—N1 | 178.93 (8) | C4—C5—C6 | 116.8 (2) |
N4—Pt1—N1 | 98.02 (9) | C4—C5—C15 | 121.0 (2) |
N3—Pt1—N2 | 98.33 (9) | C6—C5—C15 | 122.2 (2) |
N4—Pt1—N2 | 179.05 (9) | C14—C6—C5 | 118.4 (2) |
N1—Pt1—N2 | 82.67 (9) | C14—C6—C7 | 117.7 (2) |
D1OA—O1—D1OB | 108 (3) | C5—C6—C7 | 124.0 (2) |
D2OA—O2—D2OB | 105 (3) | C8—C7—C6 | 121.4 (2) |
D3OA—O3—D3OB | 103 (3) | C8—C7—H7 | 119.3 |
C1—N1—Pt1 | 109.89 (16) | C6—C7—H7 | 119.3 |
C1—N1—D1NA | 106 (2) | C7—C8—C9 | 121.6 (2) |
Pt1—N1—D1NA | 113 (2) | C7—C8—H8 | 119.2 |
C1—N1—D1NB | 112.9 (19) | C9—C8—H8 | 119.2 |
Pt1—N1—D1NB | 105.4 (19) | C13—C9—C10 | 117.8 (2) |
D1NA—N1—D1NB | 110 (3) | C13—C9—C8 | 117.7 (2) |
C2—N2—Pt1 | 110.58 (16) | C10—C9—C8 | 124.5 (2) |
C2—N2—D2NA | 106.8 (16) | C11—C10—C9 | 117.5 (2) |
Pt1—N2—D2NA | 110.3 (17) | C11—C10—C16 | 121.4 (2) |
C2—N2—D2NB | 109 (2) | C9—C10—C16 | 121.1 (2) |
Pt1—N2—D2NB | 112 (2) | C10—C11—C12 | 121.5 (2) |
D2NA—N2—D2NB | 108 (3) | C10—C11—H11 | 119.3 |
C3—N3—C14 | 118.0 (2) | C12—C11—H11 | 119.3 |
C3—N3—Pt1 | 128.42 (18) | N4—C12—C11 | 121.7 (2) |
C14—N3—Pt1 | 113.55 (16) | N4—C12—H12 | 119.1 |
C12—N4—C13 | 118.0 (2) | C11—C12—H12 | 119.1 |
C12—N4—Pt1 | 128.49 (19) | N4—C13—C9 | 123.4 (2) |
C13—N4—Pt1 | 113.43 (16) | N4—C13—C14 | 115.9 (2) |
N1—C1—C2 | 107.4 (2) | C9—C13—C14 | 120.7 (2) |
N1—C1—H1A | 110.2 | N3—C14—C6 | 123.1 (2) |
C2—C1—H1A | 110.2 | N3—C14—C13 | 116.0 (2) |
N1—C1—H1B | 110.2 | C6—C14—C13 | 120.9 (2) |
C2—C1—H1B | 110.2 | C5—C15—H15A | 109.5 |
H1A—C1—H1B | 108.5 | C5—C15—H15B | 109.5 |
N2—C2—C1 | 107.3 (2) | H15A—C15—H15B | 109.5 |
N2—C2—H2A | 110.3 | C5—C15—H15C | 109.5 |
C1—C2—H2A | 110.3 | H15A—C15—H15C | 109.5 |
N2—C2—H2B | 110.3 | H15B—C15—H15C | 109.5 |
C1—C2—H2B | 110.3 | C10—C16—H16A | 109.5 |
H2A—C2—H2B | 108.5 | C10—C16—H16B | 109.5 |
N3—C3—C4 | 121.7 (2) | H16A—C16—H16B | 109.5 |
N3—C3—H3 | 119.1 | C10—C16—H16C | 109.5 |
C4—C3—H3 | 119.1 | H16A—C16—H16C | 109.5 |
C5—C4—C3 | 121.9 (2) | H16B—C16—H16C | 109.5 |
C5—C4—H4 | 119.1 | | |
| | | |
N4—Pt1—N1—C1 | −164.76 (18) | C13—C9—C10—C11 | −0.5 (3) |
N2—Pt1—N1—C1 | 15.90 (18) | C8—C9—C10—C11 | 179.9 (2) |
N3—Pt1—N2—C2 | −167.02 (18) | C13—C9—C10—C16 | −179.9 (2) |
N1—Pt1—N2—C2 | 12.61 (19) | C8—C9—C10—C16 | 0.5 (4) |
N4—Pt1—N3—C3 | 178.5 (2) | C9—C10—C11—C12 | −0.2 (4) |
N2—Pt1—N3—C3 | −2.2 (2) | C16—C10—C11—C12 | 179.1 (2) |
N4—Pt1—N3—C14 | −3.84 (16) | C13—N4—C12—C11 | −0.4 (4) |
N2—Pt1—N3—C14 | 175.50 (17) | Pt1—N4—C12—C11 | −177.21 (19) |
N3—Pt1—N4—C12 | −179.7 (2) | C10—C11—C12—N4 | 0.7 (4) |
N1—Pt1—N4—C12 | 0.7 (2) | C12—N4—C13—C9 | −0.4 (4) |
N3—Pt1—N4—C13 | 3.36 (16) | Pt1—N4—C13—C9 | 176.87 (18) |
N1—Pt1—N4—C13 | −176.28 (17) | C12—N4—C13—C14 | −179.7 (2) |
Pt1—N1—C1—C2 | −41.0 (3) | Pt1—N4—C13—C14 | −2.4 (3) |
Pt1—N2—C2—C1 | −38.2 (3) | C10—C9—C13—N4 | 0.9 (4) |
N1—C1—C2—N2 | 51.3 (3) | C8—C9—C13—N4 | −179.5 (2) |
C14—N3—C3—C4 | −2.1 (4) | C10—C9—C13—C14 | −179.9 (2) |
Pt1—N3—C3—C4 | 175.55 (18) | C8—C9—C13—C14 | −0.3 (3) |
N3—C3—C4—C5 | 0.0 (4) | C3—N3—C14—C6 | 1.5 (4) |
C3—C4—C5—C6 | 2.6 (4) | Pt1—N3—C14—C6 | −176.42 (18) |
C3—C4—C5—C15 | −176.5 (2) | C3—N3—C14—C13 | −178.3 (2) |
C4—C5—C6—C14 | −3.0 (4) | Pt1—N3—C14—C13 | 3.7 (3) |
C15—C5—C6—C14 | 176.1 (2) | C5—C6—C14—N3 | 1.0 (4) |
C4—C5—C6—C7 | 178.0 (2) | C7—C6—C14—N3 | −179.9 (2) |
C15—C5—C6—C7 | −2.9 (4) | C5—C6—C14—C13 | −179.1 (2) |
C14—C6—C7—C8 | 0.4 (4) | C7—C6—C14—C13 | 0.0 (3) |
C5—C6—C7—C8 | 179.5 (2) | N4—C13—C14—N3 | −0.9 (3) |
C6—C7—C8—C9 | −0.7 (4) | C9—C13—C14—N3 | 179.8 (2) |
C7—C8—C9—C13 | 0.7 (4) | N4—C13—C14—C6 | 179.2 (2) |
C7—C8—C9—C10 | −179.7 (2) | C9—C13—C14—C6 | 0.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—D1OA···Cl2 | 0.86 (2) | 2.41 (2) | 3.257 (2) | 166 (3) |
O1—D1OB···Cl1 | 0.87 (2) | 2.32 (2) | 3.160 (2) | 162 (3) |
O2—D2OA···Cl1 | 0.88 (2) | 2.41 (2) | 3.284 (2) | 175 (3) |
O2—D2OB···O3 | 0.86 (2) | 1.95 (2) | 2.788 (3) | 168 (4) |
O3—D3OA···Cl1i | 0.86 (2) | 2.35 (2) | 3.177 (2) | 164 (3) |
O3—D3OB···Cl2ii | 0.86 (2) | 2.32 (2) | 3.181 (2) | 174 (3) |
N1—D1NA···Cl1i | 0.84 (3) | 2.43 (3) | 3.226 (3) | 159 (3) |
N1—D1NB···O1 | 0.93 (3) | 1.97 (3) | 2.836 (3) | 155 (3) |
N2—D2NA···Cl2i | 0.96 (3) | 2.27 (3) | 3.216 (3) | 166 (2) |
N2—D2NB···Cl2iii | 0.82 (3) | 2.61 (3) | 3.336 (2) | 149 (3) |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2. |