The neutral complex trans-[VOCl2(H2O)2] co-crystallizes with di-2-pyridylamine hydrochloride to provide the title compound, (C10H10N3)2[VCl2O(H2O)2]Cl2. The V-bound aqua ligands form two hydrogen bonds each. The amine functionality of the 2-(2-pyridylamino)pyridinium cation participates as a monovalent donor in the hydrogen bonding. In both instances, interstitial Cl- ions serve as hydrogen-bond acceptors. The three hydrogen bonds that are formed per anion give rise to one-dimensional chains along [100].
Supporting information
CCDC reference: 277713
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.097
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
turquoise
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 0.71065-0.71075
Wavelength given = 0.71093
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C16 .. 5.15 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for V1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.25
PLAT353_ALERT_3_C Long N-H Bond (0.87A) N3 - H3N ... 1.07 Ang.
PLAT353_ALERT_3_C Long N-H Bond (0.87A) N6 - H6N ... 1.07 Ang.
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.838(10) ...... 3.00 su-Rat
O2 -H2B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.838(10) ...... 3.00 su-Rat
O2 -H2B 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 2.19(3), Rep 2.189(12) ...... 2.50 su-Rat
H2A -CL3 1.555 2.566
PLAT736_ALERT_1_C H...A Calc 2.21(3), Rep 2.203(13) ...... 2.31 su-Rat
H2B -CL4 1.555 2.566
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2003 (Spek, 1990, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.
trans-Diaquadichlorooxovanadium(IV) bis[2-(2-pyridylamino)pyridinium]
dichloride
top
Crystal data top
(C10H10N3)2[VCl2O(H2O)2]Cl2 | Z = 2 |
Mr = 589.19 | F(000) = 602 |
Triclinic, P1 | Dx = 1.519 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71093 Å |
a = 7.838 (2) Å | Cell parameters from 25 reflections |
b = 9.609 (1) Å | θ = 3.2–10.1° |
c = 17.739 (3) Å | µ = 0.83 mm−1 |
α = 86.68 (1)° | T = 303 K |
β = 86.10 (2)° | Prism, turquoise |
γ = 75.32 (1)° | 0.25 × 0.15 × 0.10 mm |
V = 1288.3 (4) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 3771 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 26.0°, θmin = 1.2° |
ω/2θ scans | h = −9→3 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.735, Tmax = 0.918 | l = −21→21 |
6971 measured reflections | 3 standard reflections every 120 min |
5048 independent reflections | intensity decay: 0.1% |
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) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.4055P] where P = (Fo2 + 2Fc2)/3 |
5048 reflections | (Δ/σ)max = 0.001 |
331 parameters | Δρmax = 0.50 e Å−3 |
6 restraints | Δρmin = −0.39 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 | |
C1 | 0.2356 (3) | 0.5770 (3) | −0.00722 (14) | 0.0451 (6) | |
C2 | 0.2178 (4) | 0.7260 (3) | −0.01530 (16) | 0.0554 (7) | |
H2 | 0.2441 | 0.7761 | 0.0239 | 0.067* | |
C3 | 0.1615 (4) | 0.7960 (3) | −0.08136 (17) | 0.0626 (8) | |
H3 | 0.1504 | 0.8946 | −0.0875 | 0.075* | |
C4 | 0.1202 (5) | 0.7218 (4) | −0.13987 (17) | 0.0633 (8) | |
H4 | 0.0805 | 0.7697 | −0.1849 | 0.076* | |
C5 | 0.1394 (4) | 0.5787 (3) | −0.12967 (16) | 0.0566 (7) | |
H5 | 0.1137 | 0.5275 | −0.1685 | 0.068* | |
C6 | 0.3150 (3) | 0.3568 (3) | 0.07531 (15) | 0.0470 (6) | |
C7 | 0.3717 (4) | 0.3015 (4) | 0.14605 (17) | 0.0596 (7) | |
H7 | 0.3932 | 0.3608 | 0.1820 | 0.072* | |
C8 | 0.3948 (5) | 0.1575 (4) | 0.1610 (2) | 0.0723 (9) | |
H8 | 0.4326 | 0.1169 | 0.2078 | 0.087* | |
C9 | 0.3622 (5) | 0.0725 (4) | 0.1070 (2) | 0.0806 (10) | |
H9 | 0.3779 | −0.0260 | 0.1164 | 0.097* | |
C10 | 0.3065 (5) | 0.1355 (4) | 0.0397 (2) | 0.0737 (9) | |
H10 | 0.2851 | 0.0772 | 0.0032 | 0.088* | |
C11 | 0.3392 (3) | 0.4737 (3) | 0.44131 (14) | 0.0393 (5) | |
C12 | 0.4408 (3) | 0.4686 (3) | 0.37369 (15) | 0.0481 (6) | |
H12 | 0.4528 | 0.5531 | 0.3481 | 0.058* | |
C13 | 0.5229 (4) | 0.3377 (3) | 0.34528 (15) | 0.0497 (6) | |
H13 | 0.5929 | 0.3332 | 0.3006 | 0.060* | |
C14 | 0.5027 (3) | 0.2115 (3) | 0.38255 (15) | 0.0480 (6) | |
H14 | 0.5576 | 0.1224 | 0.3631 | 0.058* | |
C15 | 0.4014 (3) | 0.2208 (3) | 0.44783 (14) | 0.0432 (6) | |
H15 | 0.3865 | 0.1369 | 0.4732 | 0.052* | |
C16 | 0.1544 (3) | 0.6259 (3) | 0.53953 (13) | 0.0400 (5) | |
C17 | 0.0865 (3) | 0.7673 (3) | 0.56181 (15) | 0.0450 (6) | |
H17 | 0.1088 | 0.8449 | 0.5325 | 0.054* | |
C18 | −0.0131 (4) | 0.7874 (3) | 0.62793 (16) | 0.0519 (7) | |
H18 | −0.0610 | 0.8801 | 0.6444 | 0.062* | |
C19 | −0.0432 (4) | 0.6706 (3) | 0.67057 (16) | 0.0532 (7) | |
H19 | −0.1095 | 0.6832 | 0.7163 | 0.064* | |
C20 | 0.0263 (4) | 0.5357 (3) | 0.64431 (15) | 0.0503 (6) | |
H20 | 0.0040 | 0.4571 | 0.6727 | 0.060* | |
N1 | 0.2911 (3) | 0.5019 (3) | 0.05707 (13) | 0.0534 (6) | |
H1N | 0.320 (4) | 0.551 (3) | 0.0920 (18) | 0.064* | |
N2 | 0.2807 (3) | 0.2758 (3) | 0.02265 (13) | 0.0567 (6) | |
N3 | 0.1948 (3) | 0.5081 (3) | −0.06445 (12) | 0.0473 (5) | |
H3N | 0.225 (4) | 0.398 (3) | −0.0447 (16) | 0.057* | |
N4 | 0.2567 (3) | 0.6006 (2) | 0.47345 (13) | 0.0475 (5) | |
H4N | 0.272 (4) | 0.675 (3) | 0.4466 (16) | 0.057* | |
N5 | 0.1246 (3) | 0.5121 (2) | 0.57994 (12) | 0.0461 (5) | |
N6 | 0.3214 (3) | 0.3497 (2) | 0.47687 (12) | 0.0400 (4) | |
H6N | 0.245 (4) | 0.380 (3) | 0.5282 (15) | 0.048* | |
O1 | 0.2079 (3) | −0.0399 (2) | 0.75522 (11) | 0.0624 (5) | |
O2 | −0.1269 (2) | 0.1593 (3) | 0.73546 (12) | 0.0730 (7) | |
H2A | −0.180 (4) | 0.150 (4) | 0.6974 (11) | 0.088* | |
H2B | −0.203 (3) | 0.203 (4) | 0.7670 (13) | 0.088* | |
O3 | 0.3382 (3) | 0.2104 (3) | 0.72630 (11) | 0.0621 (6) | |
H3A | 0.417 (3) | 0.189 (4) | 0.6911 (11) | 0.075* | |
H3B | 0.387 (3) | 0.233 (3) | 0.7626 (11) | 0.075* | |
V1 | 0.13210 (5) | 0.12565 (4) | 0.73736 (2) | 0.03288 (11) | |
Cl1 | 0.07551 (10) | 0.23032 (9) | 0.85385 (4) | 0.0619 (2) | |
Cl2 | 0.13293 (8) | 0.14329 (7) | 0.60732 (3) | 0.04341 (15) | |
Cl3 | 0.35957 (8) | 0.86934 (6) | 0.38838 (3) | 0.04221 (15) | |
Cl4 | 0.44189 (9) | 0.67355 (8) | 0.17119 (4) | 0.0577 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0397 (13) | 0.0554 (15) | 0.0407 (13) | −0.0146 (12) | 0.0055 (11) | −0.0041 (11) |
C2 | 0.0620 (18) | 0.0618 (17) | 0.0504 (15) | −0.0298 (14) | 0.0011 (13) | −0.0082 (13) |
C3 | 0.077 (2) | 0.0527 (17) | 0.0634 (18) | −0.0289 (16) | −0.0009 (16) | 0.0040 (14) |
C4 | 0.074 (2) | 0.071 (2) | 0.0503 (16) | −0.0281 (17) | −0.0094 (15) | 0.0096 (14) |
C5 | 0.0658 (19) | 0.0634 (18) | 0.0453 (15) | −0.0230 (15) | −0.0086 (13) | −0.0025 (13) |
C6 | 0.0405 (14) | 0.0523 (15) | 0.0475 (14) | −0.0108 (12) | −0.0006 (11) | −0.0025 (11) |
C7 | 0.0583 (18) | 0.068 (2) | 0.0537 (16) | −0.0151 (15) | −0.0144 (14) | −0.0028 (14) |
C8 | 0.070 (2) | 0.073 (2) | 0.066 (2) | −0.0035 (18) | −0.0172 (17) | 0.0112 (17) |
C9 | 0.091 (3) | 0.0523 (19) | 0.091 (3) | −0.0032 (18) | −0.016 (2) | 0.0055 (18) |
C10 | 0.092 (3) | 0.0536 (19) | 0.074 (2) | −0.0105 (17) | −0.0137 (19) | −0.0147 (16) |
C11 | 0.0346 (12) | 0.0390 (13) | 0.0458 (13) | −0.0085 (10) | −0.0112 (10) | −0.0075 (10) |
C12 | 0.0458 (14) | 0.0466 (15) | 0.0547 (15) | −0.0161 (12) | −0.0092 (12) | 0.0017 (12) |
C13 | 0.0410 (14) | 0.0620 (17) | 0.0464 (14) | −0.0127 (13) | −0.0006 (11) | −0.0081 (12) |
C14 | 0.0418 (14) | 0.0466 (15) | 0.0527 (15) | −0.0030 (11) | −0.0031 (12) | −0.0147 (12) |
C15 | 0.0444 (14) | 0.0359 (12) | 0.0484 (14) | −0.0058 (11) | −0.0088 (11) | −0.0068 (10) |
C16 | 0.0371 (12) | 0.0401 (13) | 0.0437 (13) | −0.0071 (10) | −0.0105 (10) | −0.0113 (10) |
C17 | 0.0444 (14) | 0.0332 (12) | 0.0580 (15) | −0.0066 (11) | −0.0123 (12) | −0.0094 (11) |
C18 | 0.0473 (15) | 0.0424 (14) | 0.0637 (17) | −0.0004 (12) | −0.0130 (13) | −0.0218 (12) |
C19 | 0.0474 (15) | 0.0596 (17) | 0.0497 (15) | −0.0044 (13) | −0.0051 (12) | −0.0162 (13) |
C20 | 0.0573 (17) | 0.0453 (15) | 0.0470 (14) | −0.0095 (13) | −0.0046 (12) | −0.0027 (11) |
N1 | 0.0642 (15) | 0.0598 (15) | 0.0426 (12) | −0.0232 (12) | −0.0099 (11) | −0.0133 (10) |
N2 | 0.0661 (15) | 0.0523 (14) | 0.0506 (13) | −0.0098 (12) | −0.0079 (11) | −0.0099 (10) |
N3 | 0.0506 (13) | 0.0516 (13) | 0.0412 (11) | −0.0141 (10) | −0.0019 (9) | −0.0085 (9) |
N4 | 0.0559 (14) | 0.0344 (11) | 0.0534 (13) | −0.0146 (10) | −0.0011 (11) | 0.0003 (9) |
N5 | 0.0522 (13) | 0.0360 (11) | 0.0493 (12) | −0.0089 (10) | −0.0048 (10) | −0.0042 (9) |
N6 | 0.0408 (11) | 0.0360 (10) | 0.0424 (11) | −0.0062 (9) | −0.0055 (9) | −0.0064 (8) |
O1 | 0.0846 (15) | 0.0427 (11) | 0.0543 (11) | −0.0075 (10) | −0.0024 (10) | 0.0043 (8) |
O2 | 0.0316 (10) | 0.137 (2) | 0.0537 (12) | −0.0191 (12) | 0.0028 (8) | −0.0461 (13) |
O3 | 0.0466 (11) | 0.1086 (17) | 0.0476 (11) | −0.0466 (12) | 0.0054 (9) | −0.0268 (11) |
V1 | 0.0316 (2) | 0.0362 (2) | 0.0333 (2) | −0.01211 (16) | −0.00178 (15) | −0.00509 (15) |
Cl1 | 0.0529 (4) | 0.0962 (6) | 0.0468 (4) | −0.0334 (4) | 0.0070 (3) | −0.0337 (4) |
Cl2 | 0.0460 (3) | 0.0529 (4) | 0.0358 (3) | −0.0202 (3) | −0.0044 (2) | −0.0016 (2) |
Cl3 | 0.0377 (3) | 0.0454 (3) | 0.0480 (3) | −0.0176 (3) | −0.0031 (2) | −0.0057 (2) |
Cl4 | 0.0396 (3) | 0.0751 (5) | 0.0636 (4) | −0.0173 (3) | −0.0019 (3) | −0.0354 (4) |
Geometric parameters (Å, º) top
C1—N3 | 1.342 (3) | C14—C15 | 1.353 (4) |
C1—N1 | 1.350 (3) | C14—H14 | 0.9300 |
C1—C2 | 1.403 (4) | C15—N6 | 1.352 (3) |
C2—C3 | 1.360 (4) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—N5 | 1.334 (3) |
C3—C4 | 1.393 (4) | C16—N4 | 1.372 (3) |
C3—H3 | 0.9300 | C16—C17 | 1.398 (3) |
C4—C5 | 1.348 (4) | C17—C18 | 1.359 (4) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—N3 | 1.347 (3) | C18—C19 | 1.378 (4) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—N2 | 1.332 (3) | C19—C20 | 1.368 (4) |
C6—N1 | 1.381 (4) | C19—H19 | 0.9300 |
C6—C7 | 1.391 (4) | C20—N5 | 1.331 (3) |
C7—C8 | 1.362 (5) | C20—H20 | 0.9300 |
C7—H7 | 0.9300 | N1—H1N | 0.87 (3) |
C8—C9 | 1.371 (5) | N3—H3N | 1.07 (3) |
C8—H8 | 0.9300 | N4—H4N | 0.86 (3) |
C9—C10 | 1.355 (5) | N6—H6N | 1.07 (3) |
C9—H9 | 0.9300 | O1—V1 | 1.5719 (19) |
C10—N2 | 1.332 (4) | O2—V1 | 1.9753 (19) |
C10—H10 | 0.9300 | O2—H2A | 0.837 (10) |
C11—N6 | 1.350 (3) | O2—H2B | 0.838 (10) |
C11—N4 | 1.364 (3) | O3—V1 | 1.9791 (18) |
C11—C12 | 1.390 (4) | O3—H3A | 0.845 (10) |
C12—C13 | 1.367 (4) | O3—H3B | 0.839 (10) |
C12—H12 | 0.9300 | V1—Cl2 | 2.3030 (8) |
C13—C14 | 1.386 (4) | V1—Cl1 | 2.3169 (8) |
C13—H13 | 0.9300 | | |
| | | |
N3—C1—N1 | 119.4 (2) | N5—C16—N4 | 117.6 (2) |
N3—C1—C2 | 119.1 (2) | N5—C16—C17 | 122.9 (2) |
N1—C1—C2 | 121.5 (2) | N4—C16—C17 | 119.5 (2) |
C3—C2—C1 | 118.9 (3) | C18—C17—C16 | 117.6 (3) |
C3—C2—H2 | 120.6 | C18—C17—H17 | 121.2 |
C1—C2—H2 | 120.6 | C16—C17—H17 | 121.2 |
C2—C3—C4 | 120.8 (3) | C17—C18—C19 | 120.1 (2) |
C2—C3—H3 | 119.6 | C17—C18—H18 | 120.0 |
C4—C3—H3 | 119.6 | C19—C18—H18 | 120.0 |
C5—C4—C3 | 118.3 (3) | C20—C19—C18 | 118.7 (3) |
C5—C4—H4 | 120.8 | C20—C19—H19 | 120.6 |
C3—C4—H4 | 120.8 | C18—C19—H19 | 120.6 |
N3—C5—C4 | 121.5 (3) | N5—C20—C19 | 122.8 (3) |
N3—C5—H5 | 119.3 | N5—C20—H20 | 118.6 |
C4—C5—H5 | 119.3 | C19—C20—H20 | 118.6 |
N2—C6—N1 | 116.9 (2) | C1—N1—C6 | 129.6 (2) |
N2—C6—C7 | 122.9 (3) | C1—N1—H1N | 116 (2) |
N1—C6—C7 | 120.1 (3) | C6—N1—H1N | 114 (2) |
C8—C7—C6 | 117.9 (3) | C10—N2—C6 | 117.0 (3) |
C8—C7—H7 | 121.1 | C1—N3—C5 | 121.4 (2) |
C6—C7—H7 | 121.1 | C1—N3—H3N | 103.7 (15) |
C7—C8—C9 | 119.8 (3) | C5—N3—H3N | 134.8 (15) |
C7—C8—H8 | 120.1 | C11—N4—C16 | 130.0 (2) |
C9—C8—H8 | 120.1 | C11—N4—H4N | 113 (2) |
C10—C9—C8 | 118.5 (3) | C16—N4—H4N | 117 (2) |
C10—C9—H9 | 120.8 | C20—N5—C16 | 117.9 (2) |
C8—C9—H9 | 120.8 | C11—N6—C15 | 121.0 (2) |
N2—C10—C9 | 123.9 (3) | C11—N6—H6N | 105.8 (14) |
N2—C10—H10 | 118.1 | C15—N6—H6N | 133.1 (14) |
C9—C10—H10 | 118.1 | V1—O2—H2A | 124 (2) |
N6—C11—N4 | 118.5 (2) | V1—O2—H2B | 127 (2) |
N6—C11—C12 | 119.4 (2) | H2A—O2—H2B | 107.3 (16) |
N4—C11—C12 | 122.1 (2) | V1—O3—H3A | 123 (2) |
C13—C12—C11 | 119.2 (3) | V1—O3—H3B | 124 (2) |
C13—C12—H12 | 120.4 | H3A—O3—H3B | 106.1 (15) |
C11—C12—H12 | 120.4 | O1—V1—O2 | 106.87 (12) |
C12—C13—C14 | 120.6 (3) | O1—V1—O3 | 106.15 (12) |
C12—C13—H13 | 119.7 | O2—V1—O3 | 146.98 (12) |
C14—C13—H13 | 119.7 | O1—V1—Cl2 | 103.59 (8) |
C15—C14—C13 | 118.6 (2) | O2—V1—Cl2 | 86.12 (7) |
C15—C14—H14 | 120.7 | O3—V1—Cl2 | 86.13 (6) |
C13—C14—H14 | 120.7 | O1—V1—Cl1 | 105.55 (8) |
N6—C15—C14 | 121.3 (2) | O2—V1—Cl1 | 85.55 (6) |
N6—C15—H15 | 119.4 | O3—V1—Cl1 | 85.80 (6) |
C14—C15—H15 | 119.4 | Cl2—V1—Cl1 | 150.85 (3) |
| | | |
N3—C1—C2—C3 | −0.8 (4) | N3—C1—N1—C6 | 0.2 (4) |
N1—C1—C2—C3 | 180.0 (3) | C2—C1—N1—C6 | 179.4 (3) |
C1—C2—C3—C4 | 0.7 (5) | N2—C6—N1—C1 | 0.6 (4) |
C2—C3—C4—C5 | −0.7 (5) | C7—C6—N1—C1 | −179.1 (3) |
C3—C4—C5—N3 | 0.8 (5) | C9—C10—N2—C6 | 1.1 (5) |
N2—C6—C7—C8 | 0.9 (5) | N1—C6—N2—C10 | 178.9 (3) |
N1—C6—C7—C8 | −179.4 (3) | C7—C6—N2—C10 | −1.4 (4) |
C6—C7—C8—C9 | 0.0 (5) | N1—C1—N3—C5 | −179.8 (3) |
C7—C8—C9—C10 | −0.3 (6) | C2—C1—N3—C5 | 0.9 (4) |
C8—C9—C10—N2 | −0.3 (6) | C4—C5—N3—C1 | −0.9 (4) |
N6—C11—C12—C13 | −1.0 (4) | N6—C11—N4—C16 | 0.7 (4) |
N4—C11—C12—C13 | 178.7 (2) | C12—C11—N4—C16 | −179.0 (3) |
C11—C12—C13—C14 | 1.2 (4) | N5—C16—N4—C11 | −1.4 (4) |
C12—C13—C14—C15 | −0.6 (4) | C17—C16—N4—C11 | 178.5 (2) |
C13—C14—C15—N6 | −0.3 (4) | C19—C20—N5—C16 | −0.6 (4) |
N5—C16—C17—C18 | 0.3 (4) | N4—C16—N5—C20 | 179.6 (2) |
N4—C16—C17—C18 | −179.5 (2) | C17—C16—N5—C20 | −0.2 (4) |
C16—C17—C18—C19 | 0.4 (4) | N4—C11—N6—C15 | −179.5 (2) |
C17—C18—C19—C20 | −1.1 (4) | C12—C11—N6—C15 | 0.2 (3) |
C18—C19—C20—N5 | 1.2 (4) | C14—C15—N6—C11 | 0.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl4 | 0.87 (3) | 2.29 (3) | 3.149 (2) | 170 (3) |
N3—H3N···N2 | 1.07 (3) | 1.62 (3) | 2.608 (3) | 150 (2) |
N4—H4N···Cl3 | 0.86 (3) | 2.32 (3) | 3.168 (2) | 169 (3) |
N6—H6N···N5 | 1.07 (3) | 1.66 (3) | 2.624 (3) | 148 (2) |
O2—H2A···Cl3i | 0.84 (1) | 2.19 (1) | 3.016 (2) | 170 (3) |
O2—H2B···Cl4i | 0.84 (1) | 2.20 (1) | 3.026 (2) | 167 (3) |
O3—H3B···Cl4ii | 0.84 (1) | 2.22 (1) | 3.0259 (19) | 162 (3) |
O3—H3B···Cl4ii | 0.84 (1) | 2.22 (1) | 3.0259 (19) | 162 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |