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The synthesis and characterization of two new 1,3,5-triazines containing 2-(aminomethyl)-1
H-benzimidazole hydrochloride as a substituent are reported, namely, 2-{[(4,6-dichloro-1,3,5-triazin-2-yl)amino]methyl}-1
H-benzimidazol-3-ium chloride, C
11H
9Cl
2N
6+·Cl
− (
1), and bis(2,2′-{[(6-chloro-1,3,5-triazine-2,4-diyl)bis(azanediyl)]bis(methylene)}bis(1
H-benzimidazol-3-ium)) tetrachloride heptahydrate, 2C
19H
18ClN
92+·4Cl
−·7H
2O (
2). Both salts were characterized using single-crystal X-ray diffraction analysis and IR spectroscopy. Moreover, the NMR (
1H and
13C) spectra of
1 were obtained. Salts
1 and
2 have triclinic symmetry (space group
P) and their supramolecular structures are stabilized by hydrogen bonding and offset π–π interactions. In hydrated salt
2, the noncovalent interactions yield pseudo-nanotubes filled with chloride anions and water molecules, which were modelled in the refinement with substitutional and positional disorder.
Supporting information
CCDC references: 1985514; 1985513
For both structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
2-{[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]methyl}-1
H-benzimidazol-3-ium chloride (pr109_grande2_05072018)
top
Crystal data top
C11H9Cl2N6+·Cl− | Z = 2 |
Mr = 331.59 | F(000) = 336 |
Triclinic, P1 | Dx = 1.570 Mg m−3 |
a = 8.1958 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4184 (5) Å | Cell parameters from 5550 reflections |
c = 10.5965 (6) Å | θ = 3.6–25.6° |
α = 97.006 (5)° | µ = 0.65 mm−1 |
β = 104.543 (5)° | T = 293 K |
γ = 91.138 (5)° | Plate, clear light white |
V = 701.43 (7) Å3 | 0.17 × 0.15 × 0.13 mm |
Data collection top
Agilent Xcalibur Atlas Gemini diffractometer | 1929 reflections with I > 2σ(I) |
Detector resolution: 10.3659 pixels mm-1 | Rint = 0.046 |
ω scans | θmax = 25.0°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −9→9 |
Tmin = 0.653, Tmax = 1.000 | k = −10→10 |
21243 measured reflections | l = −12→12 |
2455 independent reflections | |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0347P)2 + 0.2894P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2455 reflections | Δρmax = 0.18 e Å−3 |
190 parameters | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. X-ray diffraction studies were carried out with an Xcalibur Atlas, Gemini
diffractometer with a CCD area detector and graphite monochromator (λMoκα
= 0.71073 Å). Structures 1 and 2 were solved with the OLEX2
structure solution program (Dolomanov, et al., 2009)
using SHELXS (Sheldrick, 2008) and SHELXT (Sheldrick, 2015b) respectively.
Moreover, said structures were refined with the SHELXL
(Sheldrick, 2015a) refinement package. The
non-hydrogen atoms were anisotropically refined. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.92626 (8) | 0.86334 (9) | 0.60517 (7) | 0.0664 (2) | |
Cl2 | 0.50433 (10) | 1.01755 (10) | 0.19354 (8) | 0.0726 (2) | |
N1 | 0.2585 (2) | 0.4649 (2) | 0.21225 (19) | 0.0429 (5) | |
H1 | 0.3646 (14) | 0.489 (3) | 0.242 (2) | 0.051* | |
N2 | −0.0069 (2) | 0.4535 (2) | 0.2056 (2) | 0.0447 (5) | |
H2 | −0.099 (2) | 0.473 (3) | 0.227 (2) | 0.054* | |
N3 | 0.3423 (3) | 0.6550 (3) | 0.4718 (2) | 0.0491 (5) | |
H3 | 0.362 (3) | 0.607 (3) | 0.5406 (17) | 0.059* | |
N4 | 0.6145 (2) | 0.7595 (2) | 0.53597 (18) | 0.0445 (5) | |
N5 | 0.7038 (2) | 0.9319 (2) | 0.4012 (2) | 0.0497 (5) | |
N6 | 0.4191 (2) | 0.8293 (2) | 0.34349 (18) | 0.0440 (5) | |
C1 | 0.1427 (3) | 0.5194 (3) | 0.2723 (2) | 0.0416 (5) | |
C2 | 0.1812 (3) | 0.3584 (3) | 0.1020 (2) | 0.0398 (5) | |
C3 | 0.2423 (3) | 0.2714 (3) | 0.0060 (3) | 0.0523 (6) | |
H3A | 0.356052 | 0.277898 | 0.007056 | 0.063* | |
C4 | 0.1273 (3) | 0.1751 (3) | −0.0906 (3) | 0.0588 (7) | |
H4 | 0.164334 | 0.114890 | −0.156678 | 0.071* | |
C5 | −0.0434 (3) | 0.1645 (3) | −0.0930 (3) | 0.0582 (7) | |
H5 | −0.116985 | 0.096430 | −0.159677 | 0.070* | |
C6 | −0.1053 (3) | 0.2522 (3) | 0.0007 (3) | 0.0534 (6) | |
H6 | −0.219287 | 0.246255 | −0.001128 | 0.064* | |
C7 | 0.0105 (3) | 0.3504 (3) | 0.0984 (2) | 0.0420 (5) | |
C8 | 0.1701 (3) | 0.6391 (3) | 0.3925 (3) | 0.0519 (6) | |
H8A | 0.137268 | 0.742690 | 0.366177 | 0.062* | |
H8B | 0.097204 | 0.608363 | 0.445683 | 0.062* | |
C9 | 0.4601 (3) | 0.7505 (3) | 0.4494 (2) | 0.0412 (5) | |
C10 | 0.7243 (3) | 0.8490 (3) | 0.5031 (2) | 0.0460 (6) | |
C11 | 0.5462 (3) | 0.9138 (3) | 0.3278 (2) | 0.0456 (6) | |
Cl3 | 0.65237 (7) | 0.50305 (8) | 0.26932 (6) | 0.05188 (19) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0505 (4) | 0.0743 (5) | 0.0650 (5) | −0.0059 (3) | 0.0003 (3) | 0.0043 (4) |
Cl2 | 0.0727 (5) | 0.0822 (5) | 0.0730 (5) | 0.0120 (4) | 0.0241 (4) | 0.0374 (4) |
N1 | 0.0249 (9) | 0.0558 (12) | 0.0501 (12) | 0.0039 (9) | 0.0121 (9) | 0.0098 (10) |
N2 | 0.0252 (10) | 0.0538 (12) | 0.0599 (13) | 0.0035 (9) | 0.0167 (9) | 0.0134 (10) |
N3 | 0.0490 (12) | 0.0544 (13) | 0.0469 (12) | −0.0008 (10) | 0.0162 (10) | 0.0100 (10) |
N4 | 0.0477 (12) | 0.0434 (11) | 0.0410 (11) | 0.0020 (9) | 0.0104 (9) | 0.0014 (9) |
N5 | 0.0469 (12) | 0.0478 (12) | 0.0561 (13) | −0.0025 (9) | 0.0165 (10) | 0.0070 (10) |
N6 | 0.0407 (11) | 0.0469 (11) | 0.0474 (12) | 0.0054 (9) | 0.0150 (9) | 0.0089 (9) |
C1 | 0.0324 (12) | 0.0481 (14) | 0.0493 (14) | 0.0046 (10) | 0.0163 (11) | 0.0137 (11) |
C2 | 0.0302 (11) | 0.0459 (13) | 0.0458 (13) | 0.0063 (10) | 0.0101 (10) | 0.0142 (11) |
C3 | 0.0388 (13) | 0.0673 (17) | 0.0567 (16) | 0.0158 (12) | 0.0176 (12) | 0.0171 (13) |
C4 | 0.0617 (17) | 0.0674 (18) | 0.0469 (15) | 0.0131 (14) | 0.0135 (13) | 0.0058 (13) |
C5 | 0.0516 (16) | 0.0638 (17) | 0.0530 (16) | 0.0013 (13) | 0.0029 (13) | 0.0058 (13) |
C6 | 0.0343 (13) | 0.0631 (17) | 0.0610 (16) | 0.0018 (12) | 0.0050 (12) | 0.0162 (14) |
C7 | 0.0347 (12) | 0.0465 (13) | 0.0480 (14) | 0.0070 (10) | 0.0126 (11) | 0.0141 (11) |
C8 | 0.0408 (13) | 0.0573 (16) | 0.0634 (16) | 0.0007 (11) | 0.0250 (12) | 0.0056 (13) |
C9 | 0.0438 (13) | 0.0382 (13) | 0.0439 (13) | 0.0026 (10) | 0.0174 (11) | 0.0014 (10) |
C10 | 0.0452 (14) | 0.0423 (14) | 0.0478 (14) | −0.0002 (11) | 0.0113 (11) | −0.0033 (11) |
C11 | 0.0497 (15) | 0.0426 (13) | 0.0469 (14) | 0.0074 (11) | 0.0163 (12) | 0.0061 (11) |
Cl3 | 0.0337 (3) | 0.0692 (4) | 0.0594 (4) | 0.0048 (3) | 0.0231 (3) | 0.0104 (3) |
Geometric parameters (Å, º) top
Cl1—C10 | 1.728 (2) | N6—C9 | 1.347 (3) |
Cl2—C11 | 1.724 (2) | N6—C11 | 1.306 (3) |
N1—H1 | 0.859 (10) | C1—C8 | 1.491 (3) |
N1—C1 | 1.328 (3) | C2—C3 | 1.382 (3) |
N1—C2 | 1.386 (3) | C2—C7 | 1.389 (3) |
N2—H2 | 0.852 (10) | C3—H3A | 0.9300 |
N2—C1 | 1.324 (3) | C3—C4 | 1.370 (4) |
N2—C7 | 1.382 (3) | C4—H4 | 0.9300 |
N3—H3 | 0.856 (10) | C4—C5 | 1.394 (4) |
N3—C8 | 1.444 (3) | C5—H5 | 0.9300 |
N3—C9 | 1.329 (3) | C5—C6 | 1.370 (4) |
N4—C9 | 1.358 (3) | C6—H6 | 0.9300 |
N4—C10 | 1.301 (3) | C6—C7 | 1.386 (3) |
N5—C10 | 1.334 (3) | C8—H8A | 0.9700 |
N5—C11 | 1.325 (3) | C8—H8B | 0.9700 |
| | | |
C1—N1—H1 | 123.4 (16) | C4—C5—H5 | 119.3 |
C1—N1—C2 | 109.27 (18) | C6—C5—C4 | 121.5 (3) |
C2—N1—H1 | 127.2 (16) | C6—C5—H5 | 119.3 |
C1—N2—H2 | 123.9 (17) | C5—C6—H6 | 121.7 |
C1—N2—C7 | 109.57 (18) | C5—C6—C7 | 116.7 (2) |
C7—N2—H2 | 126.5 (17) | C7—C6—H6 | 121.7 |
C8—N3—H3 | 115.6 (19) | N2—C7—C2 | 106.1 (2) |
C9—N3—H3 | 121.0 (19) | N2—C7—C6 | 132.1 (2) |
C9—N3—C8 | 123.1 (2) | C6—C7—C2 | 121.7 (2) |
C10—N4—C9 | 112.6 (2) | N3—C8—C1 | 113.84 (19) |
C11—N5—C10 | 110.9 (2) | N3—C8—H8A | 108.8 |
C11—N6—C9 | 113.1 (2) | N3—C8—H8B | 108.8 |
N1—C1—C8 | 127.1 (2) | C1—C8—H8A | 108.8 |
N2—C1—N1 | 108.9 (2) | C1—C8—H8B | 108.8 |
N2—C1—C8 | 123.94 (19) | H8A—C8—H8B | 107.7 |
N1—C2—C7 | 106.1 (2) | N3—C9—N4 | 116.6 (2) |
C3—C2—N1 | 132.6 (2) | N3—C9—N6 | 118.3 (2) |
C3—C2—C7 | 121.3 (2) | N6—C9—N4 | 125.1 (2) |
C2—C3—H3A | 121.6 | N4—C10—Cl1 | 115.95 (19) |
C4—C3—C2 | 116.8 (2) | N4—C10—N5 | 129.3 (2) |
C4—C3—H3A | 121.6 | N5—C10—Cl1 | 114.76 (18) |
C3—C4—H4 | 119.0 | N5—C11—Cl2 | 115.05 (18) |
C3—C4—C5 | 122.0 (2) | N6—C11—Cl2 | 115.98 (18) |
C5—C4—H4 | 119.0 | N6—C11—N5 | 129.0 (2) |
| | | |
N1—C1—C8—N3 | −21.4 (3) | C7—N2—C1—N1 | 0.7 (3) |
N1—C2—C3—C4 | 179.7 (2) | C7—N2—C1—C8 | 178.8 (2) |
N1—C2—C7—N2 | 0.6 (2) | C7—C2—C3—C4 | −1.2 (3) |
N1—C2—C7—C6 | −179.2 (2) | C8—N3—C9—N4 | 176.8 (2) |
N2—C1—C8—N3 | 160.9 (2) | C8—N3—C9—N6 | −3.8 (3) |
C1—N1—C2—C3 | 178.9 (2) | C9—N3—C8—C1 | 85.3 (3) |
C1—N1—C2—C7 | −0.2 (2) | C9—N4—C10—Cl1 | −178.34 (15) |
C1—N2—C7—C2 | −0.8 (2) | C9—N4—C10—N5 | 1.5 (4) |
C1—N2—C7—C6 | 178.9 (2) | C9—N6—C11—Cl2 | 179.65 (16) |
C2—N1—C1—N2 | −0.3 (3) | C9—N6—C11—N5 | −0.7 (4) |
C2—N1—C1—C8 | −178.3 (2) | C10—N4—C9—N3 | 176.7 (2) |
C2—C3—C4—C5 | 0.0 (4) | C10—N4—C9—N6 | −2.6 (3) |
C3—C2—C7—N2 | −178.6 (2) | C10—N5—C11—Cl2 | 179.39 (16) |
C3—C2—C7—C6 | 1.6 (3) | C10—N5—C11—N6 | −0.3 (4) |
C3—C4—C5—C6 | 1.0 (4) | C11—N5—C10—Cl1 | 179.67 (16) |
C4—C5—C6—C7 | −0.7 (4) | C11—N5—C10—N4 | −0.2 (4) |
C5—C6—C7—N2 | 179.7 (2) | C11—N6—C9—N3 | −177.1 (2) |
C5—C6—C7—C2 | −0.6 (4) | C11—N6—C9—N4 | 2.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl3 | 0.86 (2) | 2.30 (1) | 3.1338 (18) | 163 (2) |
N2—H2···Cl3i | 0.85 (2) | 2.21 (2) | 3.0582 (18) | 175 (2) |
N3—H3···Cl3ii | 0.86 (2) | 2.35 (2) | 3.183 (2) | 165 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1. |
Bis(2,2'-{[(6-chloro-1,3,5-triazine-2,4-diyl)bis(azanediyl)]bis(methylene)}bis(1
H-benzimidazol-3-ium)) tetrachloride heptahydrate (pr109_solucion2_16082018)
top
Crystal data top
2C19H18ClN92+·4Cl−·7H2O | Z = 2 |
Mr = 1095.75 | F(000) = 1132 |
Triclinic, P1 | Dx = 1.393 Mg m−3 |
a = 12.8675 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.1487 (5) Å | Cell parameters from 16385 reflections |
c = 16.5184 (6) Å | θ = 3.3–25.8° |
α = 75.570 (3)° | µ = 0.40 mm−1 |
β = 78.737 (3)° | T = 293 K |
γ = 64.330 (3)° | Plate, clear light white |
V = 2611.82 (17) Å3 | 0.17 × 0.14 × 0.12 mm |
Data collection top
Agilent Xcalibur Atlas Gemini diffractometer | 7312 reflections with I > 2σ(I) |
Detector resolution: 10.3659 pixels mm-1 | Rint = 0.045 |
ω scans | θmax = 26.5°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −16→16 |
Tmin = 0.723, Tmax = 1.000 | k = −17→17 |
87453 measured reflections | l = −20→20 |
10807 independent reflections | |
Refinement top
Refinement on F2 | 64 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.179 | w = 1/[σ2(Fo2) + (0.0828P)2 + 1.7651P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.007 |
10807 reflections | Δρmax = 0.57 e Å−3 |
769 parameters | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. X-ray diffraction studies were carried out with an Xcalibur Atlas, Gemini
diffractometer with a CCD area detector and graphite monochromator (λMoκα
= 0.71073 Å). Structures 1 and 2 were solved with the OLEX2
structure solution program (Dolomanov, et al., 2009)
using SHELXS (Sheldrick, 2008) and SHELXT (Sheldrick, 2015b) respectively.
Moreover, said structures were refined with the SHELXL
(Sheldrick, 2015a) refinement package. The
non-hydrogen atoms were anisotropically refined. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl2 | 0.74836 (8) | 0.33683 (6) | 0.67378 (4) | 0.0686 (2) | |
N10 | 1.0189 (2) | 0.3570 (2) | 0.18021 (15) | 0.0652 (7) | |
H10 | 1.005 (3) | 0.329 (3) | 0.1451 (19) | 0.078* | |
N11 | 1.0216 (2) | 0.3959 (2) | 0.29817 (15) | 0.0549 (6) | |
H11 | 1.018 (3) | 0.392 (3) | 0.3514 (7) | 0.066* | |
N12 | 0.9195 (2) | 0.25422 (18) | 0.39583 (14) | 0.0511 (5) | |
H12 | 0.969 (2) | 0.1984 (16) | 0.4234 (17) | 0.061* | |
N13 | 0.83551 (19) | 0.29399 (17) | 0.52587 (13) | 0.0472 (5) | |
N14 | 0.67267 (18) | 0.45751 (16) | 0.53481 (13) | 0.0430 (5) | |
N15 | 0.76184 (17) | 0.41351 (16) | 0.40009 (12) | 0.0414 (5) | |
N16 | 0.60070 (19) | 0.56775 (18) | 0.41281 (14) | 0.0481 (5) | |
H16 | 0.551 (2) | 0.6116 (19) | 0.4432 (16) | 0.058* | |
N17 | 0.7395 (2) | 0.65612 (18) | 0.20959 (14) | 0.0498 (5) | |
H17 | 0.712 (2) | 0.647 (2) | 0.1700 (14) | 0.060* | |
N18 | 0.7463 (2) | 0.67462 (19) | 0.33419 (14) | 0.0529 (6) | |
H18 | 0.728 (3) | 0.672 (3) | 0.3873 (7) | 0.063* | |
C20 | 0.9880 (2) | 0.3410 (2) | 0.26239 (17) | 0.0533 (7) | |
C21 | 1.0764 (3) | 0.4240 (3) | 0.1620 (2) | 0.0667 (9) | |
C22 | 1.1287 (3) | 0.4634 (4) | 0.0870 (2) | 0.0906 (13) | |
H22 | 1.127603 | 0.447569 | 0.035900 | 0.109* | |
C23 | 1.1816 (4) | 0.5267 (4) | 0.0933 (3) | 0.0969 (15) | |
H23 | 1.217301 | 0.554589 | 0.044770 | 0.116* | |
C24 | 1.1838 (3) | 0.5505 (3) | 0.1682 (3) | 0.0879 (12) | |
H24 | 1.221400 | 0.593477 | 0.168929 | 0.106* | |
C25 | 1.1321 (3) | 0.5127 (3) | 0.2427 (2) | 0.0730 (9) | |
H25 | 1.133277 | 0.529162 | 0.293499 | 0.088* | |
C26 | 1.0787 (2) | 0.4492 (2) | 0.23700 (19) | 0.0598 (8) | |
C27 | 0.9258 (3) | 0.2720 (2) | 0.30583 (17) | 0.0541 (7) | |
H27A | 0.847796 | 0.304849 | 0.289078 | 0.065* | |
H27B | 0.964901 | 0.203650 | 0.287753 | 0.065* | |
C28 | 0.8366 (2) | 0.32276 (19) | 0.44119 (15) | 0.0409 (5) | |
C29 | 0.7532 (2) | 0.3662 (2) | 0.56570 (16) | 0.0438 (6) | |
C30 | 0.6807 (2) | 0.47670 (19) | 0.44950 (15) | 0.0397 (5) | |
C31 | 0.6063 (2) | 0.5995 (2) | 0.32276 (17) | 0.0502 (6) | |
H31A | 0.531724 | 0.654090 | 0.307002 | 0.060* | |
H31B | 0.622922 | 0.538630 | 0.297789 | 0.060* | |
C32 | 0.6978 (2) | 0.6418 (2) | 0.28926 (16) | 0.0452 (6) | |
C33 | 0.8169 (2) | 0.7031 (2) | 0.20115 (18) | 0.0522 (7) | |
C34 | 0.8803 (3) | 0.7375 (3) | 0.1315 (2) | 0.0668 (8) | |
H34 | 0.877602 | 0.729498 | 0.077825 | 0.080* | |
C35 | 0.9469 (3) | 0.7837 (3) | 0.1460 (3) | 0.0773 (10) | |
H35 | 0.989965 | 0.808470 | 0.100734 | 0.093* | |
C36 | 0.9524 (3) | 0.7949 (3) | 0.2254 (3) | 0.0762 (10) | |
H36 | 0.999139 | 0.827068 | 0.231764 | 0.091* | |
C37 | 0.8910 (3) | 0.7602 (3) | 0.2958 (2) | 0.0664 (8) | |
H37 | 0.895572 | 0.767113 | 0.349439 | 0.080* | |
C38 | 0.8221 (2) | 0.7143 (2) | 0.28095 (18) | 0.0525 (7) | |
Cl1 | 0.34034 (6) | 0.84063 (6) | 0.38362 (4) | 0.0585 (2) | |
N1 | 0.3308 (2) | 0.98744 (18) | 0.73235 (14) | 0.0499 (5) | |
H1 | 0.339 (3) | 0.997 (2) | 0.6785 (7) | 0.060* | |
N2 | 0.2653 (2) | 0.9471 (2) | 0.86085 (14) | 0.0554 (6) | |
H2 | 0.227 (2) | 0.922 (2) | 0.9018 (14) | 0.066* | |
N3 | 0.1912 (2) | 0.92246 (18) | 0.66432 (14) | 0.0509 (5) | |
H3 | 0.138 (2) | 0.9780 (16) | 0.6394 (18) | 0.061* | |
N4 | 0.26194 (18) | 0.88149 (17) | 0.53280 (13) | 0.0468 (5) | |
N5 | 0.42493 (17) | 0.71779 (17) | 0.52059 (13) | 0.0433 (5) | |
N6 | 0.35358 (17) | 0.76924 (16) | 0.65518 (13) | 0.0426 (5) | |
N7 | 0.50763 (19) | 0.61101 (18) | 0.64051 (13) | 0.0486 (5) | |
H7 | 0.557 (2) | 0.5677 (19) | 0.6097 (16) | 0.058* | |
N8 | 0.6241 (2) | 0.7136 (2) | 0.69179 (14) | 0.0524 (6) | |
H8 | 0.637 (3) | 0.712 (2) | 0.6389 (8) | 0.063* | |
N9 | 0.5625 (2) | 0.68288 (19) | 0.82273 (14) | 0.0512 (6) | |
H9 | 0.528 (2) | 0.658 (2) | 0.8670 (13) | 0.061* | |
C1 | 0.2620 (2) | 0.9444 (2) | 0.78189 (16) | 0.0457 (6) | |
C2 | 0.3786 (2) | 1.0226 (2) | 0.78107 (18) | 0.0510 (6) | |
C3 | 0.4517 (3) | 1.0752 (2) | 0.7592 (2) | 0.0632 (8) | |
H3A | 0.481049 | 1.090813 | 0.703790 | 0.076* | |
C4 | 0.4787 (3) | 1.1030 (3) | 0.8234 (3) | 0.0744 (10) | |
H4 | 0.527785 | 1.138450 | 0.811623 | 0.089* | |
C5 | 0.4344 (3) | 1.0795 (3) | 0.9057 (3) | 0.0797 (11) | |
H5 | 0.453586 | 1.101210 | 0.947393 | 0.096* | |
C6 | 0.3633 (3) | 1.0254 (3) | 0.9284 (2) | 0.0737 (9) | |
H6 | 0.335479 | 1.008711 | 0.984023 | 0.088* | |
C7 | 0.3356 (3) | 0.9973 (2) | 0.86327 (18) | 0.0546 (7) | |
C8 | 0.1892 (2) | 0.9027 (2) | 0.75425 (17) | 0.0503 (6) | |
H8A | 0.216641 | 0.826474 | 0.775332 | 0.060* | |
H8B | 0.109928 | 0.935969 | 0.778484 | 0.060* | |
C9 | 0.2714 (2) | 0.8555 (2) | 0.61656 (16) | 0.0427 (6) | |
C10 | 0.3428 (2) | 0.8096 (2) | 0.49153 (15) | 0.0422 (6) | |
C11 | 0.4261 (2) | 0.7015 (2) | 0.60511 (15) | 0.0411 (5) | |
C12 | 0.5213 (2) | 0.5914 (2) | 0.72884 (16) | 0.0504 (6) | |
H12A | 0.573614 | 0.517579 | 0.745908 | 0.060* | |
H12B | 0.446849 | 0.602469 | 0.761268 | 0.060* | |
C13 | 0.5678 (2) | 0.6626 (2) | 0.74751 (15) | 0.0465 (6) | |
C14 | 0.6578 (2) | 0.7697 (2) | 0.73262 (18) | 0.0537 (7) | |
C15 | 0.7189 (3) | 0.8339 (3) | 0.7031 (2) | 0.0674 (8) | |
H15 | 0.743634 | 0.848697 | 0.646483 | 0.081* | |
C16 | 0.7406 (3) | 0.8741 (3) | 0.7619 (3) | 0.0773 (10) | |
H16A | 0.781691 | 0.917127 | 0.744854 | 0.093* | |
C17 | 0.7031 (3) | 0.8523 (3) | 0.8464 (3) | 0.0769 (10) | |
H17A | 0.719962 | 0.881302 | 0.884328 | 0.092* | |
C18 | 0.6417 (3) | 0.7894 (3) | 0.8761 (2) | 0.0680 (9) | |
H18A | 0.616835 | 0.774987 | 0.932747 | 0.082* | |
C19 | 0.6193 (2) | 0.7488 (2) | 0.81608 (18) | 0.0532 (7) | |
Cl4 | 0.73950 (9) | 0.38118 (10) | 0.13485 (7) | 0.0830 (5) | 0.858 (4) |
O3 | 0.6431 (4) | 0.6260 (3) | 0.0919 (2) | 0.1086 (10) | |
H3B | 0.575 (2) | 0.638 (4) | 0.117 (4) | 0.163* | |
H3C | 0.679 (4) | 0.5580 (12) | 0.108 (4) | 0.163* | |
Cl5 | 0.9384 (4) | 0.9506 (3) | 0.9281 (2) | 0.148 (2) | 0.379 (5) |
Cl3 | 0.03845 (17) | 0.39357 (17) | 0.47261 (11) | 0.1166 (9) | 0.739 (4) |
O1 | 0.4460 (3) | 0.6079 (3) | 0.96348 (17) | 0.0973 (9) | |
H1A | 0.429 (4) | 0.643 (4) | 1.002 (3) | 0.146* | |
H1B | 0.381 (2) | 0.625 (4) | 0.945 (3) | 0.146* | |
O5 | 0.0851 (3) | 0.0538 (2) | 0.4337 (3) | 0.1043 (11) | 0.876 (3) |
H5A | 0.142 (4) | 0.015 (4) | 0.463 (4) | 0.156* | 0.876 (3) |
H5B | 0.065 (5) | 0.008 (4) | 0.423 (4) | 0.156* | 0.876 (3) |
Cl5A | 0.1261 (10) | 0.1083 (8) | 0.4767 (8) | 0.121 (3) | 0.124 (3) |
Cl6 | 0.7129 (5) | 0.7248 (5) | 0.5061 (3) | 0.0929 (15) | 0.539 (9) |
O6 | 0.6969 (16) | 0.6973 (14) | 0.5172 (9) | 0.086 (3) | 0.461 (9) |
Cl7 | 0.6211 (4) | 0.9358 (4) | 0.4565 (2) | 0.1184 (15) | 0.533 (10) |
O7 | 0.6033 (12) | 0.9805 (11) | 0.4309 (8) | 0.124 (3) | 0.467 (10) |
O8A | 1.0106 (7) | 0.2004 (9) | 0.0900 (4) | 0.094 (2) | 0.542 (10) |
O8 | 0.9966 (8) | 0.2728 (10) | 0.0670 (5) | 0.100 (2) | 0.458 (10) |
Cl9 | 0.6213 (7) | 0.2970 (6) | 0.8753 (4) | 0.1097 (18) | 0.429 (10) |
O9 | 0.6212 (14) | 0.2614 (11) | 0.8942 (9) | 0.119 (3) | 0.571 (10) |
Cl10 | 0.1383 (5) | 0.9650 (4) | 0.1677 (3) | 0.1483 (19) | 0.437 (5) |
O10 | 0.1962 (9) | 0.9048 (8) | 0.2149 (5) | 0.151 (2) | 0.563 (5) |
O2 | 0.9641 (2) | 0.0855 (2) | 0.63765 (18) | 0.0881 (8) | |
H2A | 0.932 (4) | 0.142 (2) | 0.603 (2) | 0.132* | |
H2B | 0.914 (3) | 0.087 (4) | 0.6799 (18) | 0.132* | |
O4 | 0.1657 (5) | 0.8569 (5) | −0.0004 (3) | 0.180 (2) | |
H4A | 0.198 (7) | 0.863 (7) | 0.037 (5) | 0.271* | |
H4B | 0.106 (5) | 0.917 (4) | −0.008 (6) | 0.271* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl2 | 0.0924 (6) | 0.0611 (4) | 0.0379 (4) | −0.0183 (4) | −0.0047 (3) | −0.0101 (3) |
N10 | 0.0633 (16) | 0.0742 (18) | 0.0410 (14) | −0.0145 (14) | 0.0034 (11) | −0.0131 (12) |
N11 | 0.0529 (13) | 0.0573 (14) | 0.0433 (13) | −0.0162 (11) | 0.0042 (11) | −0.0087 (11) |
N12 | 0.0526 (13) | 0.0470 (13) | 0.0429 (12) | −0.0112 (10) | 0.0017 (10) | −0.0116 (10) |
N13 | 0.0537 (13) | 0.0422 (11) | 0.0400 (12) | −0.0161 (10) | −0.0012 (9) | −0.0066 (9) |
N14 | 0.0454 (11) | 0.0429 (11) | 0.0391 (11) | −0.0183 (10) | 0.0034 (9) | −0.0100 (9) |
N15 | 0.0418 (11) | 0.0445 (11) | 0.0375 (11) | −0.0189 (9) | 0.0019 (9) | −0.0091 (9) |
N16 | 0.0456 (12) | 0.0482 (13) | 0.0407 (12) | −0.0113 (10) | −0.0004 (9) | −0.0087 (9) |
N17 | 0.0547 (13) | 0.0532 (13) | 0.0400 (12) | −0.0193 (11) | −0.0044 (10) | −0.0114 (10) |
N18 | 0.0616 (14) | 0.0583 (14) | 0.0404 (12) | −0.0250 (12) | −0.0057 (11) | −0.0101 (11) |
C20 | 0.0469 (15) | 0.0551 (16) | 0.0415 (14) | −0.0061 (13) | 0.0036 (11) | −0.0142 (12) |
C21 | 0.0493 (16) | 0.0669 (19) | 0.0516 (18) | −0.0054 (15) | 0.0053 (13) | 0.0022 (14) |
C22 | 0.076 (2) | 0.101 (3) | 0.055 (2) | −0.016 (2) | 0.0086 (17) | 0.0061 (19) |
C23 | 0.073 (2) | 0.087 (3) | 0.084 (3) | −0.020 (2) | 0.012 (2) | 0.025 (2) |
C24 | 0.062 (2) | 0.075 (2) | 0.098 (3) | −0.0222 (18) | 0.002 (2) | 0.016 (2) |
C25 | 0.0550 (18) | 0.0623 (19) | 0.081 (2) | −0.0169 (16) | 0.0006 (16) | 0.0038 (17) |
C26 | 0.0453 (15) | 0.0554 (17) | 0.0550 (18) | −0.0086 (13) | 0.0044 (13) | 0.0011 (13) |
C27 | 0.0555 (16) | 0.0555 (16) | 0.0441 (15) | −0.0147 (13) | 0.0045 (12) | −0.0190 (12) |
C28 | 0.0442 (13) | 0.0417 (13) | 0.0393 (13) | −0.0216 (11) | 0.0030 (10) | −0.0095 (10) |
C29 | 0.0530 (15) | 0.0427 (13) | 0.0386 (13) | −0.0233 (12) | −0.0011 (11) | −0.0077 (11) |
C30 | 0.0416 (13) | 0.0433 (13) | 0.0385 (13) | −0.0227 (11) | 0.0021 (10) | −0.0094 (10) |
C31 | 0.0508 (15) | 0.0528 (15) | 0.0434 (14) | −0.0171 (13) | −0.0082 (11) | −0.0072 (12) |
C32 | 0.0494 (14) | 0.0399 (13) | 0.0405 (14) | −0.0116 (11) | −0.0072 (11) | −0.0076 (10) |
C33 | 0.0489 (15) | 0.0483 (15) | 0.0512 (16) | −0.0132 (12) | −0.0040 (12) | −0.0080 (12) |
C34 | 0.0632 (19) | 0.070 (2) | 0.0585 (19) | −0.0253 (17) | 0.0012 (15) | −0.0055 (15) |
C35 | 0.062 (2) | 0.073 (2) | 0.085 (3) | −0.0296 (18) | 0.0019 (18) | 0.0023 (19) |
C36 | 0.061 (2) | 0.0586 (19) | 0.110 (3) | −0.0263 (16) | −0.0123 (19) | −0.0101 (19) |
C37 | 0.0647 (19) | 0.0589 (18) | 0.079 (2) | −0.0245 (16) | −0.0138 (17) | −0.0147 (16) |
C38 | 0.0528 (15) | 0.0453 (14) | 0.0552 (17) | −0.0151 (13) | −0.0083 (13) | −0.0088 (12) |
Cl1 | 0.0644 (4) | 0.0726 (5) | 0.0367 (3) | −0.0278 (4) | −0.0075 (3) | −0.0052 (3) |
N1 | 0.0559 (13) | 0.0502 (13) | 0.0412 (12) | −0.0195 (11) | −0.0002 (10) | −0.0116 (10) |
N2 | 0.0630 (15) | 0.0639 (15) | 0.0402 (13) | −0.0290 (12) | 0.0016 (10) | −0.0104 (11) |
N3 | 0.0500 (13) | 0.0465 (12) | 0.0476 (13) | −0.0081 (10) | −0.0077 (10) | −0.0134 (10) |
N4 | 0.0477 (12) | 0.0483 (12) | 0.0431 (12) | −0.0158 (10) | −0.0109 (9) | −0.0082 (10) |
N5 | 0.0425 (11) | 0.0503 (12) | 0.0381 (11) | −0.0179 (10) | −0.0027 (9) | −0.0129 (9) |
N6 | 0.0436 (11) | 0.0448 (11) | 0.0374 (11) | −0.0143 (9) | −0.0042 (9) | −0.0108 (9) |
N7 | 0.0487 (13) | 0.0483 (13) | 0.0385 (12) | −0.0072 (10) | −0.0048 (9) | −0.0135 (9) |
N8 | 0.0477 (12) | 0.0651 (15) | 0.0361 (12) | −0.0165 (11) | −0.0037 (10) | −0.0077 (11) |
N9 | 0.0558 (14) | 0.0535 (13) | 0.0359 (12) | −0.0151 (11) | −0.0023 (10) | −0.0087 (10) |
C1 | 0.0488 (14) | 0.0404 (13) | 0.0415 (14) | −0.0132 (11) | 0.0002 (11) | −0.0092 (11) |
C2 | 0.0488 (15) | 0.0434 (14) | 0.0551 (16) | −0.0123 (12) | −0.0055 (12) | −0.0111 (12) |
C3 | 0.0573 (17) | 0.0529 (17) | 0.076 (2) | −0.0199 (14) | −0.0083 (15) | −0.0102 (15) |
C4 | 0.063 (2) | 0.0575 (19) | 0.105 (3) | −0.0224 (16) | −0.0225 (19) | −0.0122 (19) |
C5 | 0.080 (2) | 0.072 (2) | 0.093 (3) | −0.0197 (19) | −0.036 (2) | −0.025 (2) |
C6 | 0.084 (2) | 0.080 (2) | 0.058 (2) | −0.027 (2) | −0.0186 (17) | −0.0176 (17) |
C7 | 0.0568 (16) | 0.0517 (16) | 0.0513 (16) | −0.0162 (13) | −0.0094 (13) | −0.0101 (12) |
C8 | 0.0516 (15) | 0.0469 (14) | 0.0487 (15) | −0.0165 (12) | 0.0046 (12) | −0.0164 (12) |
C9 | 0.0434 (13) | 0.0436 (13) | 0.0449 (14) | −0.0187 (11) | −0.0055 (11) | −0.0116 (11) |
C10 | 0.0442 (13) | 0.0510 (14) | 0.0369 (13) | −0.0240 (12) | −0.0065 (10) | −0.0068 (11) |
C11 | 0.0405 (13) | 0.0449 (13) | 0.0394 (13) | −0.0172 (11) | −0.0027 (10) | −0.0118 (10) |
C12 | 0.0525 (15) | 0.0501 (15) | 0.0384 (14) | −0.0115 (12) | −0.0064 (11) | −0.0067 (11) |
C13 | 0.0421 (13) | 0.0485 (14) | 0.0350 (13) | −0.0070 (11) | −0.0053 (10) | −0.0039 (11) |
C14 | 0.0441 (14) | 0.0546 (16) | 0.0521 (16) | −0.0105 (13) | −0.0074 (12) | −0.0079 (13) |
C15 | 0.0564 (18) | 0.066 (2) | 0.072 (2) | −0.0219 (16) | −0.0056 (15) | −0.0059 (16) |
C16 | 0.063 (2) | 0.061 (2) | 0.106 (3) | −0.0227 (17) | −0.015 (2) | −0.012 (2) |
C17 | 0.070 (2) | 0.064 (2) | 0.098 (3) | −0.0170 (18) | −0.021 (2) | −0.0280 (19) |
C18 | 0.073 (2) | 0.0653 (19) | 0.0606 (19) | −0.0149 (17) | −0.0124 (16) | −0.0217 (15) |
C19 | 0.0518 (15) | 0.0488 (15) | 0.0502 (16) | −0.0096 (13) | −0.0093 (12) | −0.0110 (12) |
Cl4 | 0.0713 (7) | 0.1053 (9) | 0.0624 (7) | −0.0393 (6) | −0.0106 (5) | 0.0107 (5) |
O3 | 0.147 (3) | 0.132 (3) | 0.0769 (19) | −0.074 (2) | −0.0199 (19) | −0.0312 (18) |
Cl5 | 0.187 (5) | 0.099 (3) | 0.099 (3) | −0.009 (2) | −0.017 (2) | −0.0065 (19) |
Cl3 | 0.1299 (15) | 0.1631 (18) | 0.0857 (11) | −0.0798 (13) | −0.0021 (9) | −0.0413 (11) |
O1 | 0.110 (2) | 0.138 (3) | 0.0630 (17) | −0.077 (2) | −0.0056 (15) | −0.0044 (16) |
O5 | 0.106 (3) | 0.0685 (19) | 0.114 (3) | −0.0011 (17) | −0.034 (2) | −0.0192 (18) |
Cl5A | 0.113 (5) | 0.084 (4) | 0.126 (5) | −0.004 (4) | −0.024 (4) | −0.008 (4) |
Cl6 | 0.115 (2) | 0.130 (3) | 0.0419 (14) | −0.0598 (17) | 0.0091 (11) | −0.0246 (16) |
O6 | 0.106 (5) | 0.117 (6) | 0.054 (4) | −0.067 (4) | 0.006 (3) | −0.020 (4) |
Cl7 | 0.171 (3) | 0.098 (3) | 0.065 (2) | −0.055 (2) | 0.0237 (17) | −0.0066 (15) |
O7 | 0.173 (5) | 0.105 (5) | 0.072 (5) | −0.057 (5) | 0.016 (4) | 0.003 (4) |
O8A | 0.097 (3) | 0.164 (7) | 0.055 (3) | −0.079 (5) | 0.002 (3) | −0.034 (4) |
O8 | 0.097 (3) | 0.161 (7) | 0.057 (4) | −0.054 (6) | 0.000 (3) | −0.045 (4) |
Cl9 | 0.130 (2) | 0.130 (4) | 0.069 (2) | −0.068 (3) | 0.0128 (19) | −0.008 (2) |
O9 | 0.142 (4) | 0.140 (7) | 0.086 (5) | −0.067 (5) | −0.017 (4) | −0.018 (4) |
Cl10 | 0.209 (4) | 0.191 (4) | 0.109 (3) | −0.153 (4) | −0.017 (2) | −0.003 (2) |
O10 | 0.218 (6) | 0.178 (5) | 0.106 (4) | −0.136 (5) | −0.019 (3) | −0.004 (3) |
O2 | 0.0716 (16) | 0.0784 (17) | 0.0848 (18) | 0.0011 (13) | −0.0210 (13) | −0.0129 (14) |
O4 | 0.189 (4) | 0.282 (6) | 0.104 (3) | −0.164 (5) | 0.011 (3) | 0.016 (3) |
Geometric parameters (Å, º) top
Cl2—C29 | 1.724 (3) | N3—H3 | 0.859 (10) |
N10—H10 | 0.858 (10) | N3—C8 | 1.439 (3) |
N10—C20 | 1.329 (4) | N3—C9 | 1.339 (3) |
N10—C21 | 1.384 (5) | N4—C9 | 1.356 (3) |
N11—H11 | 0.861 (10) | N4—C10 | 1.316 (3) |
N11—C20 | 1.326 (4) | N5—C10 | 1.317 (3) |
N11—C26 | 1.392 (4) | N5—C11 | 1.359 (3) |
N12—H12 | 0.859 (10) | N6—C9 | 1.331 (3) |
N12—C27 | 1.437 (4) | N6—C11 | 1.339 (3) |
N12—C28 | 1.339 (3) | N7—H7 | 0.856 (10) |
N13—C28 | 1.355 (3) | N7—C11 | 1.336 (3) |
N13—C29 | 1.313 (3) | N7—C12 | 1.447 (3) |
N14—C29 | 1.312 (3) | N8—H8 | 0.861 (10) |
N14—C30 | 1.359 (3) | N8—C13 | 1.324 (4) |
N15—C28 | 1.336 (3) | N8—C14 | 1.398 (4) |
N15—C30 | 1.333 (3) | N9—H9 | 0.861 (10) |
N16—H16 | 0.856 (10) | N9—C13 | 1.326 (3) |
N16—C30 | 1.339 (3) | N9—C19 | 1.388 (4) |
N16—C31 | 1.440 (3) | C1—C8 | 1.488 (4) |
N17—H17 | 0.856 (10) | C2—C3 | 1.383 (4) |
N17—C32 | 1.322 (3) | C2—C7 | 1.383 (4) |
N17—C33 | 1.387 (4) | C3—H3A | 0.9300 |
N18—H18 | 0.859 (10) | C3—C4 | 1.369 (5) |
N18—C32 | 1.326 (3) | C4—H4 | 0.9300 |
N18—C38 | 1.391 (4) | C4—C5 | 1.385 (5) |
C20—C27 | 1.487 (4) | C5—H5 | 0.9300 |
C21—C22 | 1.397 (5) | C5—C6 | 1.376 (5) |
C21—C26 | 1.380 (5) | C6—H6 | 0.9300 |
C22—H22 | 0.9300 | C6—C7 | 1.389 (4) |
C22—C23 | 1.371 (7) | C8—H8A | 0.9700 |
C23—H23 | 0.9300 | C8—H8B | 0.9700 |
C23—C24 | 1.370 (6) | C12—H12A | 0.9700 |
C24—H24 | 0.9300 | C12—H12B | 0.9700 |
C24—C25 | 1.379 (5) | C12—C13 | 1.490 (4) |
C25—H25 | 0.9300 | C14—C15 | 1.388 (4) |
C25—C26 | 1.376 (5) | C14—C19 | 1.375 (4) |
C27—H27A | 0.9700 | C15—H15 | 0.9300 |
C27—H27B | 0.9700 | C15—C16 | 1.364 (5) |
C31—H31A | 0.9700 | C16—H16A | 0.9300 |
C31—H31B | 0.9700 | C16—C17 | 1.389 (5) |
C31—C32 | 1.497 (4) | C17—H17A | 0.9300 |
C33—C34 | 1.388 (4) | C17—C18 | 1.377 (5) |
C33—C38 | 1.384 (4) | C18—H18A | 0.9300 |
C34—H34 | 0.9300 | C18—C19 | 1.391 (4) |
C34—C35 | 1.364 (5) | O3—H3B | 0.858 (10) |
C35—H35 | 0.9300 | O3—H3C | 0.864 (10) |
C35—C36 | 1.379 (5) | Cl5—O8Ai | 2.028 (11) |
C36—H36 | 0.9300 | Cl5—Cl10ii | 1.886 (6) |
C36—C37 | 1.382 (5) | O1—H1A | 0.844 (10) |
C37—H37 | 0.9300 | O1—H1B | 0.854 (10) |
C37—C38 | 1.391 (4) | O5—H5A | 0.857 (10) |
Cl1—C10 | 1.729 (2) | O5—H5B | 0.856 (10) |
N1—H1 | 0.858 (10) | Cl10—O10 | 1.110 (9) |
N1—C1 | 1.326 (3) | O2—H2A | 0.848 (10) |
N1—C2 | 1.389 (4) | O2—H2B | 0.850 (10) |
N2—H2 | 0.855 (10) | O4—H4A | 0.853 (10) |
N2—C1 | 1.324 (3) | O4—H4B | 0.862 (10) |
N2—C7 | 1.381 (4) | | |
| | | |
C20—N10—H10 | 124 (3) | C1—N2—C7 | 109.4 (2) |
C20—N10—C21 | 108.9 (3) | C7—N2—H2 | 128 (2) |
C21—N10—H10 | 127 (3) | C8—N3—H3 | 120 (2) |
C20—N11—H11 | 125 (2) | C9—N3—H3 | 117 (2) |
C20—N11—C26 | 109.3 (3) | C9—N3—C8 | 122.7 (2) |
C26—N11—H11 | 125 (2) | C10—N4—C9 | 112.6 (2) |
C27—N12—H12 | 121 (2) | C10—N5—C11 | 112.4 (2) |
C28—N12—H12 | 116 (2) | C9—N6—C11 | 114.6 (2) |
C28—N12—C27 | 122.4 (2) | C11—N7—H7 | 120 (2) |
C29—N13—C28 | 113.1 (2) | C11—N7—C12 | 120.6 (2) |
C29—N14—C30 | 112.6 (2) | C12—N7—H7 | 119 (2) |
C30—N15—C28 | 114.5 (2) | C13—N8—H8 | 124 (2) |
C30—N16—H16 | 119 (2) | C13—N8—C14 | 109.2 (2) |
C30—N16—C31 | 120.9 (2) | C14—N8—H8 | 126 (2) |
C31—N16—H16 | 119 (2) | C13—N9—H9 | 123 (2) |
C32—N17—H17 | 123 (2) | C13—N9—C19 | 109.2 (2) |
C32—N17—C33 | 109.0 (2) | C19—N9—H9 | 128 (2) |
C33—N17—H17 | 127 (2) | N1—C1—C8 | 126.2 (2) |
C32—N18—H18 | 122 (2) | N2—C1—N1 | 109.0 (2) |
C32—N18—C38 | 109.0 (2) | N2—C1—C8 | 124.7 (2) |
C38—N18—H18 | 129 (2) | C3—C2—N1 | 131.3 (3) |
N10—C20—C27 | 124.6 (3) | C3—C2—C7 | 122.5 (3) |
N11—C20—N10 | 109.1 (3) | C7—C2—N1 | 106.1 (2) |
N11—C20—C27 | 126.3 (2) | C2—C3—H3A | 121.8 |
N10—C21—C22 | 132.3 (4) | C4—C3—C2 | 116.4 (3) |
C26—C21—N10 | 106.9 (3) | C4—C3—H3A | 121.8 |
C26—C21—C22 | 120.8 (4) | C3—C4—H4 | 119.3 |
C21—C22—H22 | 122.0 | C3—C4—C5 | 121.3 (3) |
C23—C22—C21 | 116.1 (4) | C5—C4—H4 | 119.3 |
C23—C22—H22 | 122.0 | C4—C5—H5 | 118.6 |
C22—C23—H23 | 118.7 | C6—C5—C4 | 122.7 (3) |
C24—C23—C22 | 122.5 (4) | C6—C5—H5 | 118.6 |
C24—C23—H23 | 118.7 | C5—C6—H6 | 122.0 |
C23—C24—H24 | 118.9 | C5—C6—C7 | 116.0 (3) |
C23—C24—C25 | 122.1 (4) | C7—C6—H6 | 122.0 |
C25—C24—H24 | 118.9 | N2—C7—C2 | 106.3 (2) |
C24—C25—H25 | 122.1 | N2—C7—C6 | 132.7 (3) |
C26—C25—C24 | 115.8 (4) | C2—C7—C6 | 120.9 (3) |
C26—C25—H25 | 122.1 | N3—C8—C1 | 112.7 (2) |
C21—C26—N11 | 105.8 (3) | N3—C8—H8A | 109.1 |
C25—C26—N11 | 131.4 (3) | N3—C8—H8B | 109.1 |
C25—C26—C21 | 122.7 (3) | C1—C8—H8A | 109.1 |
N12—C27—C20 | 113.4 (2) | C1—C8—H8B | 109.1 |
N12—C27—H27A | 108.9 | H8A—C8—H8B | 107.8 |
N12—C27—H27B | 108.9 | N3—C9—N4 | 117.1 (2) |
C20—C27—H27A | 108.9 | N6—C9—N3 | 117.4 (2) |
C20—C27—H27B | 108.9 | N6—C9—N4 | 125.5 (2) |
H27A—C27—H27B | 107.7 | N4—C10—Cl1 | 115.13 (19) |
N12—C28—N13 | 116.8 (2) | N4—C10—N5 | 129.3 (2) |
N15—C28—N12 | 118.1 (2) | N5—C10—Cl1 | 115.55 (19) |
N15—C28—N13 | 125.1 (2) | N6—C11—N5 | 125.4 (2) |
N13—C29—Cl2 | 115.86 (19) | N7—C11—N5 | 117.0 (2) |
N14—C29—Cl2 | 115.11 (19) | N7—C11—N6 | 117.7 (2) |
N14—C29—N13 | 129.0 (2) | N7—C12—H12A | 109.2 |
N15—C30—N14 | 125.5 (2) | N7—C12—H12B | 109.2 |
N15—C30—N16 | 118.0 (2) | N7—C12—C13 | 112.0 (2) |
N16—C30—N14 | 116.5 (2) | H12A—C12—H12B | 107.9 |
N16—C31—H31A | 109.3 | C13—C12—H12A | 109.2 |
N16—C31—H31B | 109.3 | C13—C12—H12B | 109.2 |
N16—C31—C32 | 111.5 (2) | N8—C13—N9 | 109.0 (3) |
H31A—C31—H31B | 108.0 | N8—C13—C12 | 125.3 (2) |
C32—C31—H31A | 109.3 | N9—C13—C12 | 125.6 (2) |
C32—C31—H31B | 109.3 | C15—C14—N8 | 131.8 (3) |
N17—C32—N18 | 109.4 (2) | C19—C14—N8 | 106.0 (3) |
N17—C32—C31 | 125.1 (2) | C19—C14—C15 | 122.2 (3) |
N18—C32—C31 | 125.4 (2) | C14—C15—H15 | 121.8 |
N17—C33—C34 | 132.0 (3) | C16—C15—C14 | 116.3 (3) |
C38—C33—N17 | 106.5 (2) | C16—C15—H15 | 121.8 |
C38—C33—C34 | 121.5 (3) | C15—C16—H16A | 119.1 |
C33—C34—H34 | 121.8 | C15—C16—C17 | 121.8 (4) |
C35—C34—C33 | 116.4 (3) | C17—C16—H16A | 119.1 |
C35—C34—H34 | 121.8 | C16—C17—H17A | 118.9 |
C34—C35—H35 | 118.9 | C18—C17—C16 | 122.3 (3) |
C34—C35—C36 | 122.3 (3) | C18—C17—H17A | 118.9 |
C36—C35—H35 | 118.9 | C17—C18—H18A | 122.1 |
C35—C36—H36 | 118.8 | C17—C18—C19 | 115.9 (3) |
C35—C36—C37 | 122.4 (3) | C19—C18—H18A | 122.0 |
C37—C36—H36 | 118.8 | N9—C19—C18 | 131.8 (3) |
C36—C37—H37 | 122.3 | C14—C19—N9 | 106.7 (3) |
C36—C37—C38 | 115.3 (3) | C14—C19—C18 | 121.5 (3) |
C38—C37—H37 | 122.3 | H3B—O3—H3C | 102.1 (16) |
N18—C38—C37 | 131.9 (3) | Cl10ii—Cl5—O8Ai | 103.1 (3) |
C33—C38—N18 | 106.0 (2) | H1A—O1—H1B | 104.6 (16) |
C33—C38—C37 | 122.1 (3) | H5A—O5—H5B | 103.2 (16) |
C1—N1—H1 | 125 (2) | O10—Cl10—Cl5ii | 168.2 (7) |
C1—N1—C2 | 109.1 (2) | H2A—O2—H2B | 105.4 (16) |
C2—N1—H1 | 126 (2) | H4A—O4—H4B | 103.2 (16) |
C1—N2—H2 | 122 (2) | | |
| | | |
N10—C20—C27—N12 | 170.3 (3) | N1—C1—C8—N3 | −5.6 (4) |
N10—C21—C22—C23 | −178.1 (3) | N1—C2—C3—C4 | 177.1 (3) |
N10—C21—C26—N11 | −0.1 (3) | N1—C2—C7—N2 | 0.7 (3) |
N10—C21—C26—C25 | 178.3 (3) | N1—C2—C7—C6 | −177.6 (3) |
N11—C20—C27—N12 | −9.5 (4) | N2—C1—C8—N3 | 172.3 (2) |
N16—C31—C32—N17 | 165.2 (2) | N7—C12—C13—N8 | −20.1 (4) |
N16—C31—C32—N18 | −17.6 (4) | N7—C12—C13—N9 | 162.0 (2) |
N17—C33—C34—C35 | 178.2 (3) | N8—C14—C15—C16 | −177.7 (3) |
N17—C33—C38—N18 | −0.7 (3) | N8—C14—C19—N9 | −0.9 (3) |
N17—C33—C38—C37 | −179.2 (3) | N8—C14—C19—C18 | 177.7 (3) |
C20—N10—C21—C22 | 178.2 (3) | C1—N1—C2—C3 | −177.7 (3) |
C20—N10—C21—C26 | −0.4 (3) | C1—N1—C2—C7 | 0.6 (3) |
C20—N11—C26—C21 | 0.6 (3) | C1—N2—C7—C2 | −1.8 (3) |
C20—N11—C26—C25 | −177.6 (3) | C1—N2—C7—C6 | 176.2 (3) |
C21—N10—C20—N11 | 0.8 (3) | C2—N1—C1—N2 | −1.8 (3) |
C21—N10—C20—C27 | −179.1 (3) | C2—N1—C1—C8 | 176.3 (2) |
C21—C22—C23—C24 | 0.1 (6) | C2—C3—C4—C5 | −0.1 (5) |
C22—C21—C26—N11 | −178.9 (3) | C3—C2—C7—N2 | 179.2 (3) |
C22—C21—C26—C25 | −0.5 (5) | C3—C2—C7—C6 | 0.8 (4) |
C22—C23—C24—C25 | −0.4 (6) | C3—C4—C5—C6 | 1.4 (5) |
C23—C24—C25—C26 | 0.3 (5) | C4—C5—C6—C7 | −1.5 (5) |
C24—C25—C26—N11 | 178.1 (3) | C5—C6—C7—N2 | −177.5 (3) |
C24—C25—C26—C21 | 0.1 (4) | C5—C6—C7—C2 | 0.4 (5) |
C26—N11—C20—N10 | −0.9 (3) | C7—N2—C1—N1 | 2.3 (3) |
C26—N11—C20—C27 | 179.0 (3) | C7—N2—C1—C8 | −175.9 (2) |
C26—C21—C22—C23 | 0.4 (5) | C7—C2—C3—C4 | −1.0 (4) |
C27—N12—C28—N13 | 176.0 (2) | C8—N3—C9—N4 | 178.2 (2) |
C27—N12—C28—N15 | −4.0 (4) | C8—N3—C9—N6 | −1.9 (4) |
C28—N12—C27—C20 | 84.8 (3) | C9—N3—C8—C1 | 87.6 (3) |
C28—N13—C29—Cl2 | −178.46 (18) | C9—N4—C10—Cl1 | −177.05 (18) |
C28—N13—C29—N14 | 2.5 (4) | C9—N4—C10—N5 | 3.0 (4) |
C28—N15—C30—N14 | 2.8 (4) | C9—N6—C11—N5 | 3.9 (4) |
C28—N15—C30—N16 | −178.2 (2) | C9—N6—C11—N7 | −177.2 (2) |
C29—N13—C28—N12 | 178.8 (2) | C10—N4—C9—N3 | −178.4 (2) |
C29—N13—C28—N15 | −1.3 (4) | C10—N4—C9—N6 | 1.7 (4) |
C29—N14—C30—N15 | −1.8 (4) | C10—N5—C11—N6 | −0.1 (4) |
C29—N14—C30—N16 | 179.2 (2) | C10—N5—C11—N7 | −179.0 (2) |
C30—N14—C29—Cl2 | 179.86 (17) | C11—N5—C10—Cl1 | 176.34 (18) |
C30—N14—C29—N13 | −1.1 (4) | C11—N5—C10—N4 | −3.7 (4) |
C30—N15—C28—N12 | 178.9 (2) | C11—N6—C9—N3 | 175.3 (2) |
C30—N15—C28—N13 | −1.1 (4) | C11—N6—C9—N4 | −4.8 (4) |
C30—N16—C31—C32 | −75.9 (3) | C11—N7—C12—C13 | −69.6 (3) |
C31—N16—C30—N14 | 175.4 (2) | C12—N7—C11—N5 | 174.8 (2) |
C31—N16—C30—N15 | −3.7 (4) | C12—N7—C11—N6 | −4.2 (4) |
C32—N17—C33—C34 | −177.5 (3) | C13—N8—C14—C15 | 179.4 (3) |
C32—N17—C33—C38 | 1.4 (3) | C13—N8—C14—C19 | 0.4 (3) |
C32—N18—C38—C33 | −0.3 (3) | C13—N9—C19—C14 | 1.1 (3) |
C32—N18—C38—C37 | 178.1 (3) | C13—N9—C19—C18 | −177.3 (3) |
C33—N17—C32—N18 | −1.6 (3) | C14—N8—C13—N9 | 0.3 (3) |
C33—N17—C32—C31 | 176.0 (2) | C14—N8—C13—C12 | −178.0 (2) |
C33—C34—C35—C36 | 0.7 (5) | C14—C15—C16—C17 | −0.4 (5) |
C34—C33—C38—N18 | 178.4 (3) | C15—C14—C19—N9 | 180.0 (3) |
C34—C33—C38—C37 | −0.2 (4) | C15—C14—C19—C18 | −1.4 (4) |
C34—C35—C36—C37 | 0.0 (5) | C15—C16—C17—C18 | −0.1 (5) |
C35—C36—C37—C38 | −0.8 (5) | C16—C17—C18—C19 | −0.1 (5) |
C36—C37—C38—N18 | −177.3 (3) | C17—C18—C19—N9 | 179.1 (3) |
C36—C37—C38—C33 | 0.9 (4) | C17—C18—C19—C14 | 0.8 (4) |
C38—N18—C32—N17 | 1.1 (3) | C19—N9—C13—N8 | −0.9 (3) |
C38—N18—C32—C31 | −176.4 (2) | C19—N9—C13—C12 | 177.4 (2) |
C38—C33—C34—C35 | −0.6 (4) | C19—C14—C15—C16 | 1.1 (4) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl7ii | 0.86 (1) | 2.25 (2) | 3.071 (4) | 160 (3) |
O1—H1A···O9iii | 0.84 (5) | 2.27 (5) | 3.112 (15) | 179 (6) |
O1—H1B···Cl4iv | 0.86 (4) | 2.26 (4) | 3.071 (4) | 156 (5) |
N2—H2···O4v | 0.85 (2) | 1.86 (2) | 2.709 (6) | 171 (3) |
O2—H2A···N13 | 0.85 (3) | 2.18 (3) | 3.016 (3) | 174 (4) |
O2—H2B···O10iv | 0.85 (4) | 2.49 (3) | 3.256 (6) | 151 (4) |
N3—H3···O2vi | 0.86 (2) | 2.09 (3) | 2.866 (4) | 150 (3) |
O3—H3B···O9iv | 0.86 (5) | 2.32 (5) | 3.056 (19) | 145 (5) |
O3—H3C···Cl4 | 0.86 (3) | 2.23 (2) | 3.072 (4) | 166 (6) |
O4—H4A···O9iv | 0.85 (10) | 2.51 (10) | 3.136 (19) | 132 (7) |
O5—H5A···N4vii | 0.85 (6) | 2.09 (6) | 2.909 (4) | 161 (5) |
O5—H5B···O2viii | 0.86 (6) | 2.03 (6) | 2.864 (5) | 163 (6) |
N7—H7···N14 | 0.85 (3) | 2.10 (3) | 2.953 (3) | 177 (3) |
N8—H8···Cl6 | 0.86 (1) | 2.22 (2) | 3.047 (5) | 162 (4) |
N9—H9···O1 | 0.86 (2) | 1.89 (2) | 2.751 (4) | 178 (2) |
N10—H10···O8A | 0.86 (4) | 2.20 (4) | 3.009 (11) | 157 (3) |
N11—H11···Cl3ix | 0.86 (1) | 2.08 (2) | 2.923 (3) | 168 (4) |
N12—H12···O5ix | 0.86 (2) | 1.93 (2) | 2.716 (4) | 152 (2) |
N16—H16···N5 | 0.86 (3) | 2.14 (3) | 2.990 (3) | 178 (3) |
N17—H17···O3 | 0.86 (3) | 1.85 (3) | 2.704 (5) | 175 (3) |
N18—H18···Cl6 | 0.86 (1) | 2.21 (2) | 3.003 (6) | 153 (3) |
C8—H8A···Cl4iv | 0.97 | 2.81 | 3.759 (3) | 168 |
C12—H12B···Cl4iv | 0.97 | 2.62 | 3.583 (3) | 173 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1; (vi) x−1, y+1, z; (vii) x, y−1, z; (viii) −x+1, −y, −z+1; (ix) x+1, y, z. |
π–π interactions geometry (Å) for compounds
1 and 2 topCompound | Cg(i); Cg(j) | Cg(i)···Cg(j) (Å) | Symmetry code |
1 | i = 1; j = 3 | 3.5637 (15) | -x, -y+1, -z |
1 | i = 2; j = 2 | 3.3905 (12) | -x+1, -y+2, -z+1 |
2 | i = 2; j = 10 | 3.5502 (19) | -x+1, -y+2, -z+1 |
2 | i = 2; j = 9 | 3.554 (2) | -x+2, -y+1, -z+1 |
2 | i = 3; j = 8 | 3.6767 (15) | -x+1, -y+1, -z+1 |
2 | i = 4; j = 5 | 3.818 (2) | x, y, z |
2 | i = 4; j = 7 | 3.6781 (18) | -x+1, -y+2, -z+1 |
2 | i = 4; j = 10 | 3.724 (2) | -x+1, -y+2, -z+1 |
2 | i = 5; j = 6 | 3.550 (2) | -x+2, -y+1, -z+1 |
2 | i = 5; j = 9 | 3.823 (2) | -x+2, -y+1, -z+1 |
2 | i = 9; j = 10 | 3.826 (2) | x, y, z |
Cg is the centre of gravity of a ring. |
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