The crystal structure of the double salt tetrakis(anilinium) hexachlorotin(IV) dichloride, (C
6H
8N)
4[SnCl
6]Cl
2, exhibits alternating inorganic and organic layers parallel to the
ab plane. In the inorganic layer, ammonium groups interact with chloride anions and isolated tilted [SnCl
6]
2− octahedra through N—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 236054
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.104
- Data-to-parameter ratio = 31.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C7 -C12 1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C13 -C18 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2000).
Tetrakis(anilinium) hexachlorotin(IV) dichloride
top
Crystal data top
(C6H8N)4[SnCl6]Cl2 | F(000) = 1560 |
Mr = 778.83 | Dx = 1.541 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 185 reflections |
a = 15.615 (4) Å | θ = 2–32° |
b = 10.543 (4) Å | µ = 1.42 mm−1 |
c = 20.403 (5) Å | T = 293 K |
β = 92.40 (2)° | Block, light brown |
V = 3355.9 (17) Å3 | 0.50 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Oxford Excalibur2 diffractometer | 10736 independent reflections |
Radiation source: fine-focus sealed tube | 5357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω–2θ scans | θmax = 31.9°, θmin = 4.0° |
Absorption correction: multi-scan (Blessing, 1995) | h = −22→22 |
Tmin = 0.532, Tmax = 0.757 | k = −12→15 |
30679 measured reflections | l = −29→29 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0411P)2] where P = (Fo2 + 2Fc2)/3 |
10736 reflections | (Δ/σ)max = 0.005 |
338 parameters | Δρmax = 1.02 e Å−3 |
60 restraints | Δρmin = −0.58 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 | |
N2 | 0.25134 (19) | −0.1246 (2) | −0.16768 (12) | 0.0504 (7) | |
H2A | 0.2065 | −0.0920 | −0.1901 | 0.076* | |
H2B | 0.2477 | −0.2088 | −0.1680 | 0.076* | |
H2C | 0.2994 | −0.1008 | −0.1862 | 0.076* | |
N3 | 0.25710 (19) | 0.1214 (2) | 0.68417 (12) | 0.0523 (7) | |
H3A | 0.2625 | 0.2054 | 0.6863 | 0.078* | |
H3B | 0.3016 | 0.0851 | 0.7054 | 0.078* | |
H3C | 0.2089 | 0.0982 | 0.7026 | 0.078* | |
N1 | 0.4587 (2) | 0.8032 (3) | 0.19859 (15) | 0.0636 (9) | |
H1C | 0.4941 | 0.8628 | 0.2145 | 0.095* | |
H1A | 0.4653 | 0.7328 | 0.2223 | 0.095* | |
H1B | 0.4048 | 0.8302 | 0.2004 | 0.095* | |
N4 | 0.00100 (19) | 0.2450 (3) | 0.30654 (14) | 0.0648 (9) | |
H4A | 0.0067 | 0.1651 | 0.2932 | 0.097* | |
H4B | 0.0449 | 0.2909 | 0.2933 | 0.097* | |
H4C | −0.0478 | 0.2769 | 0.2896 | 0.097* | |
C24 | 0.0383 (2) | 0.3470 (3) | 0.41180 (19) | 0.0546 (9) | |
H24 | 0.0646 | 0.4118 | 0.3892 | 0.066* | |
C19 | −0.0002 (2) | 0.2482 (3) | 0.37854 (17) | 0.0450 (8) | |
C23 | 0.0374 (2) | 0.3491 (4) | 0.4793 (2) | 0.0636 (11) | |
H23 | 0.0634 | 0.4154 | 0.5027 | 0.076* | |
C22 | −0.0020 (2) | 0.2531 (4) | 0.5117 (2) | 0.0675 (11) | |
H22 | −0.0030 | 0.2552 | 0.5573 | 0.081* | |
C20 | −0.0396 (2) | 0.1518 (3) | 0.41058 (19) | 0.0550 (9) | |
H20 | −0.0658 | 0.0857 | 0.3872 | 0.066* | |
C21 | −0.0397 (3) | 0.1547 (4) | 0.4785 (2) | 0.0638 (11) | |
H21 | −0.0655 | 0.0896 | 0.5012 | 0.077* | |
Cl7 | 0.10229 (5) | 0.00270 (8) | 0.75179 (4) | 0.0504 (2) | |
Cl8 | 0.58691 (6) | 0.02214 (9) | 0.23994 (5) | 0.0609 (3) | |
C1 | 0.4781 (2) | 0.7764 (3) | 0.13001 (18) | 0.0496 (9) | |
C2 | 0.5265 (3) | 0.6724 (4) | 0.1173 (2) | 0.0722 (12) | |
H2 | 0.5478 | 0.6211 | 0.1513 | 0.087* | |
C3 | 0.5429 (3) | 0.6452 (4) | 0.0538 (3) | 0.0849 (14) | |
H3 | 0.5750 | 0.5736 | 0.0445 | 0.102* | |
C4 | 0.5134 (3) | 0.7210 (5) | 0.0036 (2) | 0.0839 (14) | |
H4 | 0.5258 | 0.7020 | −0.0395 | 0.101* | |
C6 | 0.4469 (3) | 0.8535 (4) | 0.0819 (2) | 0.0666 (11) | |
H6 | 0.4139 | 0.9237 | 0.0920 | 0.080* | |
C5 | 0.4643 (3) | 0.8271 (4) | 0.0178 (2) | 0.0769 (12) | |
H5 | 0.4435 | 0.8797 | −0.0158 | 0.092* | |
Sn | 0.230329 (14) | −0.00050 (2) | 0.257819 (10) | 0.03698 (7) | |
Cl1 | 0.12090 (5) | −0.10126 (8) | 0.32113 (4) | 0.0527 (2) | |
Cl2 | 0.34470 (5) | 0.09625 (8) | 0.19576 (4) | 0.0500 (2) | |
Cl5 | 0.23704 (6) | −0.19009 (7) | 0.18993 (4) | 0.0516 (2) | |
Cl6 | 0.34200 (5) | −0.09639 (7) | 0.33004 (4) | 0.0457 (2) | |
Cl4 | 0.22586 (6) | 0.18760 (8) | 0.32433 (4) | 0.0554 (2) | |
C16 | 0.2473 (2) | 0.0041 (4) | 0.48740 (17) | 0.0557 (9) | |
H16 | 0.2455 | −0.0216 | 0.4438 | 0.067* | |
C13 | 0.2543 (2) | 0.0810 (3) | 0.61508 (15) | 0.0400 (7) | |
C15 | 0.2930 (3) | −0.0643 (4) | 0.53349 (19) | 0.0626 (11) | |
H15 | 0.3217 | −0.1373 | 0.5212 | 0.075* | |
C14 | 0.2970 (3) | −0.0261 (3) | 0.59813 (18) | 0.0557 (10) | |
H14 | 0.3282 | −0.0725 | 0.6296 | 0.067* | |
C18 | 0.2067 (2) | 0.1487 (3) | 0.56973 (17) | 0.0566 (10) | |
H18 | 0.1764 | 0.2200 | 0.5823 | 0.068* | |
C17 | 0.2041 (3) | 0.1105 (4) | 0.50532 (18) | 0.0615 (10) | |
H17 | 0.1728 | 0.1571 | 0.4739 | 0.074* | |
Cl3 | 0.12225 (6) | 0.08995 (9) | 0.18308 (4) | 0.0550 (2) | |
C10 | 0.2499 (3) | 0.0069 (4) | 0.02631 (18) | 0.0631 (10) | |
H10 | 0.2493 | 0.0364 | 0.0693 | 0.076* | |
C8 | 0.2916 (2) | 0.0344 (3) | −0.08414 (18) | 0.0535 (9) | |
H8 | 0.3189 | 0.0810 | −0.1158 | 0.064* | |
C7 | 0.2521 (2) | −0.0784 (3) | −0.09941 (15) | 0.0407 (7) | |
C9 | 0.2895 (3) | 0.0765 (4) | −0.0204 (2) | 0.0658 (11) | |
H9 | 0.3153 | 0.1533 | −0.0089 | 0.079* | |
C11 | 0.2118 (3) | −0.1045 (4) | 0.00994 (17) | 0.0608 (10) | |
H11 | 0.1854 | −0.1518 | 0.0419 | 0.073* | |
C12 | 0.2119 (2) | −0.1486 (3) | −0.05360 (17) | 0.0532 (9) | |
H12 | 0.1851 | −0.2247 | −0.0651 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N2 | 0.067 (2) | 0.0447 (16) | 0.0391 (16) | 0.0066 (14) | 0.0030 (14) | −0.0021 (12) |
N3 | 0.070 (2) | 0.0429 (16) | 0.0449 (17) | −0.0045 (14) | 0.0095 (15) | −0.0036 (13) |
N1 | 0.060 (2) | 0.064 (2) | 0.067 (2) | −0.0042 (16) | 0.0062 (17) | −0.0076 (17) |
N4 | 0.064 (2) | 0.072 (2) | 0.058 (2) | −0.0167 (17) | 0.0000 (16) | 0.0010 (17) |
C24 | 0.053 (2) | 0.042 (2) | 0.069 (3) | −0.0071 (16) | 0.0014 (19) | 0.0013 (18) |
C19 | 0.0381 (19) | 0.0433 (19) | 0.053 (2) | 0.0006 (15) | −0.0002 (16) | 0.0013 (16) |
C23 | 0.055 (2) | 0.060 (2) | 0.075 (3) | 0.005 (2) | −0.007 (2) | −0.023 (2) |
C22 | 0.055 (2) | 0.089 (3) | 0.059 (3) | 0.014 (2) | 0.004 (2) | −0.003 (2) |
C20 | 0.051 (2) | 0.048 (2) | 0.067 (3) | −0.0077 (17) | 0.0010 (19) | −0.0044 (18) |
C21 | 0.061 (3) | 0.065 (3) | 0.066 (3) | −0.005 (2) | 0.015 (2) | 0.014 (2) |
Cl7 | 0.0432 (4) | 0.0510 (5) | 0.0571 (5) | 0.0009 (4) | 0.0016 (4) | −0.0087 (4) |
Cl8 | 0.0458 (5) | 0.0752 (7) | 0.0616 (6) | −0.0024 (4) | 0.0021 (4) | −0.0162 (5) |
C1 | 0.042 (2) | 0.047 (2) | 0.060 (2) | −0.0044 (16) | 0.0068 (17) | −0.0091 (18) |
C2 | 0.057 (3) | 0.065 (3) | 0.096 (4) | 0.018 (2) | 0.017 (2) | 0.011 (2) |
C3 | 0.082 (3) | 0.070 (3) | 0.105 (4) | 0.021 (3) | 0.032 (3) | −0.007 (3) |
C4 | 0.089 (4) | 0.098 (4) | 0.067 (3) | −0.022 (3) | 0.030 (3) | −0.020 (3) |
C6 | 0.067 (3) | 0.052 (2) | 0.081 (3) | 0.016 (2) | 0.006 (2) | −0.003 (2) |
C5 | 0.077 (3) | 0.085 (3) | 0.069 (3) | 0.001 (3) | 0.001 (2) | 0.008 (3) |
Sn | 0.04106 (12) | 0.03370 (11) | 0.03631 (11) | 0.00154 (10) | 0.00331 (8) | 0.00081 (9) |
Cl1 | 0.0470 (5) | 0.0606 (5) | 0.0512 (5) | −0.0022 (4) | 0.0096 (4) | 0.0107 (4) |
Cl2 | 0.0494 (5) | 0.0439 (5) | 0.0577 (5) | −0.0007 (4) | 0.0157 (4) | 0.0037 (4) |
Cl5 | 0.0682 (6) | 0.0422 (5) | 0.0440 (5) | −0.0023 (4) | −0.0002 (4) | −0.0100 (4) |
Cl6 | 0.0464 (5) | 0.0418 (4) | 0.0480 (5) | 0.0002 (4) | −0.0072 (4) | 0.0001 (4) |
Cl4 | 0.0747 (6) | 0.0406 (5) | 0.0509 (5) | 0.0081 (4) | 0.0050 (5) | −0.0101 (4) |
C16 | 0.060 (2) | 0.065 (2) | 0.0424 (19) | −0.002 (2) | 0.0073 (17) | −0.008 (2) |
C13 | 0.0468 (19) | 0.0350 (17) | 0.0384 (18) | −0.0048 (14) | 0.0060 (15) | 0.0004 (14) |
C15 | 0.067 (3) | 0.055 (2) | 0.066 (3) | 0.015 (2) | 0.006 (2) | −0.015 (2) |
C14 | 0.070 (3) | 0.044 (2) | 0.052 (2) | 0.0128 (17) | −0.0067 (19) | −0.0020 (16) |
C18 | 0.071 (3) | 0.048 (2) | 0.051 (2) | 0.0212 (19) | 0.006 (2) | −0.0019 (17) |
C17 | 0.074 (3) | 0.063 (3) | 0.047 (2) | 0.016 (2) | −0.0038 (19) | 0.0030 (19) |
Cl3 | 0.0497 (5) | 0.0650 (6) | 0.0497 (5) | 0.0078 (4) | −0.0026 (4) | 0.0139 (4) |
C10 | 0.065 (3) | 0.082 (3) | 0.042 (2) | 0.007 (2) | −0.0042 (18) | −0.015 (2) |
C8 | 0.063 (2) | 0.043 (2) | 0.056 (2) | −0.0036 (17) | 0.0129 (19) | −0.0040 (16) |
C7 | 0.0467 (19) | 0.0374 (18) | 0.0376 (18) | 0.0105 (15) | −0.0011 (15) | 0.0024 (14) |
C9 | 0.064 (3) | 0.052 (2) | 0.081 (3) | −0.007 (2) | 0.001 (2) | −0.026 (2) |
C11 | 0.070 (3) | 0.073 (3) | 0.040 (2) | −0.004 (2) | 0.0051 (19) | 0.0056 (19) |
C12 | 0.064 (2) | 0.046 (2) | 0.049 (2) | −0.0087 (17) | −0.0012 (18) | 0.0025 (17) |
Geometric parameters (Å, º) top
N2—C7 | 1.475 (4) | C4—C5 | 1.393 (6) |
N2—H2A | 0.8900 | C4—H4 | 0.9300 |
N2—H2B | 0.8900 | C6—C5 | 1.374 (5) |
N2—H2C | 0.8900 | C6—H6 | 0.9300 |
N3—C13 | 1.472 (4) | C5—H5 | 0.9300 |
N3—H3A | 0.8900 | Sn—Cl4 | 2.4057 (10) |
N3—H3B | 0.8900 | Sn—Cl3 | 2.4223 (10) |
N3—H3C | 0.8900 | Sn—Cl1 | 2.4292 (10) |
N1—C1 | 1.472 (4) | Sn—Cl5 | 2.4366 (10) |
N1—H1C | 0.8900 | Sn—Cl6 | 2.4533 (10) |
N1—H1A | 0.8900 | Sn—Cl2 | 2.4541 (10) |
N1—H1B | 0.8900 | C16—C15 | 1.363 (5) |
N4—C19 | 1.470 (4) | C16—C17 | 1.367 (5) |
N4—H4A | 0.8900 | C16—H16 | 0.9300 |
N4—H4B | 0.8900 | C13—C14 | 1.363 (4) |
N4—H4C | 0.8900 | C13—C18 | 1.364 (4) |
C24—C19 | 1.368 (4) | C15—C14 | 1.378 (5) |
C24—C23 | 1.378 (5) | C15—H15 | 0.9300 |
C24—H24 | 0.9300 | C14—H14 | 0.9300 |
C19—C20 | 1.369 (4) | C18—C17 | 1.373 (4) |
C23—C22 | 1.370 (5) | C18—H18 | 0.9300 |
C23—H23 | 0.9300 | C17—H17 | 0.9300 |
C22—C21 | 1.359 (5) | C10—C11 | 1.353 (5) |
C22—H22 | 0.9300 | C10—C9 | 1.370 (5) |
C20—C21 | 1.386 (5) | C10—H10 | 0.9300 |
C20—H20 | 0.9300 | C8—C7 | 1.369 (4) |
C21—H21 | 0.9300 | C8—C9 | 1.376 (5) |
C1—C6 | 1.350 (5) | C8—H8 | 0.9300 |
C1—C2 | 1.362 (5) | C7—C12 | 1.365 (4) |
C2—C3 | 1.362 (5) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.377 (4) |
C3—C4 | 1.363 (6) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
| | | |
C7—N2—H2A | 109.5 | C5—C6—H6 | 120.3 |
C7—N2—H2B | 109.5 | C6—C5—C4 | 119.5 (4) |
H2A—N2—H2B | 109.5 | C6—C5—H5 | 120.3 |
C7—N2—H2C | 109.5 | C4—C5—H5 | 120.3 |
H2A—N2—H2C | 109.5 | Cl4—Sn—Cl3 | 89.70 (4) |
H2B—N2—H2C | 109.5 | Cl4—Sn—Cl1 | 91.31 (4) |
C13—N3—H3A | 109.5 | Cl3—Sn—Cl1 | 91.14 (4) |
C13—N3—H3B | 109.5 | Cl4—Sn—Cl5 | 179.12 (3) |
H3A—N3—H3B | 109.5 | Cl3—Sn—Cl5 | 90.60 (4) |
C13—N3—H3C | 109.5 | Cl1—Sn—Cl5 | 89.51 (4) |
H3A—N3—H3C | 109.5 | Cl4—Sn—Cl6 | 92.15 (3) |
H3B—N3—H3C | 109.5 | Cl3—Sn—Cl6 | 177.85 (3) |
C1—N1—H1C | 109.5 | Cl1—Sn—Cl6 | 89.92 (3) |
C1—N1—H1A | 109.5 | Cl5—Sn—Cl6 | 87.53 (3) |
H1C—N1—H1A | 109.5 | Cl4—Sn—Cl2 | 89.28 (4) |
C1—N1—H1B | 109.5 | Cl3—Sn—Cl2 | 90.83 (4) |
H1C—N1—H1B | 109.5 | Cl1—Sn—Cl2 | 177.95 (3) |
H1A—N1—H1B | 109.5 | Cl5—Sn—Cl2 | 89.89 (3) |
C19—N4—H4A | 109.5 | Cl6—Sn—Cl2 | 88.10 (3) |
C19—N4—H4B | 109.5 | C15—C16—C17 | 120.0 (3) |
H4A—N4—H4B | 109.5 | C15—C16—H16 | 120.0 |
C19—N4—H4C | 109.5 | C17—C16—H16 | 120.0 |
H4A—N4—H4C | 109.5 | C14—C13—C18 | 121.3 (3) |
H4B—N4—H4C | 109.5 | C14—C13—N3 | 119.2 (3) |
C19—C24—C23 | 119.0 (3) | C18—C13—N3 | 119.5 (3) |
C19—C24—H24 | 120.5 | C16—C15—C14 | 120.4 (3) |
C23—C24—H24 | 120.5 | C16—C15—H15 | 119.8 |
C24—C19—C20 | 121.7 (3) | C14—C15—H15 | 119.8 |
C24—C19—N4 | 119.3 (3) | C13—C14—C15 | 118.8 (3) |
C20—C19—N4 | 119.0 (3) | C13—C14—H14 | 120.6 |
C22—C23—C24 | 119.6 (4) | C15—C14—H14 | 120.6 |
C22—C23—H23 | 120.2 | C13—C18—C17 | 119.3 (3) |
C24—C23—H23 | 120.2 | C13—C18—H18 | 120.3 |
C21—C22—C23 | 121.1 (4) | C17—C18—H18 | 120.3 |
C21—C22—H22 | 119.4 | C16—C17—C18 | 120.1 (3) |
C23—C22—H22 | 119.4 | C16—C17—H17 | 120.0 |
C19—C20—C21 | 118.7 (3) | C18—C17—H17 | 120.0 |
C19—C20—H20 | 120.7 | C11—C10—C9 | 120.0 (3) |
C21—C20—H20 | 120.7 | C11—C10—H10 | 120.0 |
C22—C21—C20 | 119.8 (4) | C9—C10—H10 | 120.0 |
C22—C21—H21 | 120.1 | C7—C8—C9 | 117.8 (3) |
C20—C21—H21 | 120.1 | C7—C8—H8 | 121.1 |
C6—C1—C2 | 122.2 (4) | C9—C8—H8 | 121.1 |
C6—C1—N1 | 119.6 (3) | C12—C7—C8 | 122.0 (3) |
C2—C1—N1 | 118.3 (4) | C12—C7—N2 | 118.8 (3) |
C1—C2—C3 | 118.6 (4) | C8—C7—N2 | 119.1 (3) |
C1—C2—H2 | 120.7 | C10—C9—C8 | 120.9 (3) |
C3—C2—H2 | 120.7 | C10—C9—H9 | 119.5 |
C2—C3—C4 | 121.3 (4) | C8—C9—H9 | 119.5 |
C2—C3—H3 | 119.4 | C10—C11—C12 | 120.5 (4) |
C4—C3—H3 | 119.4 | C10—C11—H11 | 119.7 |
C3—C4—C5 | 119.1 (4) | C12—C11—H11 | 119.7 |
C3—C4—H4 | 120.4 | C7—C12—C11 | 118.7 (3) |
C5—C4—H4 | 120.4 | C7—C12—H12 | 120.7 |
C1—C6—C5 | 119.3 (4) | C11—C12—H12 | 120.7 |
C1—C6—H6 | 120.3 | | |
| | | |
C23—C24—C19—C20 | 0.2 (5) | C17—C16—C15—C14 | −0.9 (6) |
C23—C24—C19—N4 | −179.6 (3) | C18—C13—C14—C15 | 1.4 (6) |
C19—C24—C23—C22 | −0.3 (6) | N3—C13—C14—C15 | 179.1 (3) |
C24—C23—C22—C21 | 0.6 (6) | C16—C15—C14—C13 | 0.2 (6) |
C24—C19—C20—C21 | −0.5 (5) | C14—C13—C18—C17 | −2.2 (6) |
N4—C19—C20—C21 | 179.3 (3) | N3—C13—C18—C17 | −179.8 (3) |
C23—C22—C21—C20 | −0.9 (6) | C15—C16—C17—C18 | 0.1 (6) |
C19—C20—C21—C22 | 0.9 (6) | C13—C18—C17—C16 | 1.4 (6) |
C6—C1—C2—C3 | −0.6 (6) | C9—C8—C7—C12 | −0.3 (5) |
N1—C1—C2—C3 | 178.4 (4) | C9—C8—C7—N2 | 178.5 (3) |
C1—C2—C3—C4 | 1.2 (7) | C11—C10—C9—C8 | −0.3 (6) |
C2—C3—C4—C5 | −1.0 (7) | C7—C8—C9—C10 | 0.7 (6) |
C2—C1—C6—C5 | −0.2 (6) | C9—C10—C11—C12 | −0.4 (6) |
N1—C1—C6—C5 | −179.2 (4) | C8—C7—C12—C11 | −0.5 (5) |
C1—C6—C5—C4 | 0.4 (7) | N2—C7—C12—C11 | −179.2 (3) |
C3—C4—C5—C6 | 0.1 (7) | C10—C11—C12—C7 | 0.8 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl7i | 0.89 | 2.21 | 3.098 (3) | 175 |
N2—H2B···Cl6ii | 0.89 | 2.53 | 3.266 (3) | 141 |
N2—H2B···Cl1ii | 0.89 | 2.82 | 3.538 (3) | 139 |
N2—H2C···Cl8iii | 0.89 | 2.28 | 3.167 (3) | 173 |
N3—H3A···Cl2iv | 0.89 | 2.46 | 3.280 (3) | 154 |
N3—H3B···Cl8v | 0.89 | 2.32 | 3.210 (3) | 176 |
N3—H3C···Cl7 | 0.89 | 2.22 | 3.097 (3) | 168 |
N1—H1C···Cl8vi | 0.89 | 2.26 | 3.148 (3) | 172 |
N1—H1A···Cl8vii | 0.89 | 2.50 | 3.307 (3) | 151 |
N1—H1B···Cl5vi | 0.89 | 2.63 | 3.459 (3) | 156 |
N4—H4A···Cl7viii | 0.89 | 2.60 | 3.267 (3) | 133 |
N4—H4B···Cl7ix | 0.89 | 2.51 | 3.313 (3) | 150 |
N4—H4C···Cl1x | 0.89 | 2.80 | 3.553 (3) | 143 |
Symmetry codes: (i) x, y, z−1; (ii) x, −y−1/2, z−1/2; (iii) −x+1, −y, −z; (iv) x, −y+1/2, z+1/2; (v) −x+1, −y, −z+1; (vi) x, y+1, z; (vii) −x+1, y+1/2, −z+1/2; (viii) −x, −y, −z+1; (ix) x, −y+1/2, z−1/2; (x) −x, y+1/2, −z+1/2. |