research communications
Crystal structures of pure 3-(4-bromo-2-chlorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one and contaminated with 3-(4-bromophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one
aFaculty of Pharmacy, Department of Pharmaceutical Chemistry, Alazhar University-Gaza, Gaza Strip, Palestinian Territories, bFaculty of Science, Chemistry Department, Islamic University of Gaza Strip, Gaza Strip, Palestinian Territories, cDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany, dHochschule Furtwangen (HFU), Fakultät Medical and Life Sciences, Jakob-Kienzle Strasse 17, 78054 Villingen-Schwenningen, Germany, and eFraunhofer IZI, EXIM Rostock, Perlickstrasse 1, 04103 Leipzig, Germany
*Correspondence e-mail: deigner@gmx.de
The side product of the cyclocondensation reaction between ethyl benzimidazole-2-carboxylate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromophenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by π–π interactions.
1. Chemical context
Compounds containing a benzimidazole core have been tackled in the area of pharmaceuticals (Karpin'ska et al. 2011; Singh et al. (2010) and therapeutic areas (Biron, 2006; Pescovitz, 2008), as well as commercial drugs such as omeprazole (prilosec), pantoprazole (protonix), vermox and mibefradil (Karpińska et al., 2011). Several benzimidazole-based compounds show anti-cancer activity (Thomas et al., 2007), and some of them exhibit cytotoxic effects against a panel of human cancer cell lines (Refaat, 2010). For example, benzimidazole-4,7-diones exhibit cytotoxicity against colon, breast and lung cell lines (Gellis et al., 2008). The good efficiency of imidazole-based compounds as anti-cancer agents promoted this study of synthesizing a masked benzimidazole in a triazine ring as a new scaffold with potential anti-cancer candidates. The first and the second derivative of this series afforded good crystals and have been published previously (Abu Thaher et al., 2016a,b). The aim of this study was to prepare 3-(4-bromophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]-triazin-4(3H)-one.
2. Structural commentary
During crystallization of the product from a bi-solvent mixture of n-heptane and EtAc, two types of crystals were obtained. The biggest and highest quality blocks among them, (1) (Fig. 1), were obtained as a of the target compound and a side product containing a chlorine atom in position 2 of the bromophenyl group. The chlorine atom in it is attached to the bromophenyl group as a side product obtained during preparation of the starting material, namely hydrazonoyl chloride, via chlorination of the corresponding hydrazone. The quantitative ratio between the side:target product is 1:7. The second type of crystals, (2), nice column-like crystals, turned out to contain the pure side product (Fig. 2). Furthermore, crystals of (2) contain two independent molecules (A and B) in the Their geometry is almost identical but different from (1) (see Table 1). The r.m.s. fit of all non-hydrogen atoms from molecule A onto B is 0.116 Å. The fused 13-membered ring system in (1) and (2) is nearly planar with an r.m.s. deviation of 0.025 Å in (1) and an r.m.s. deviation of 0.100 Å for molecule A and 0.089 Å for molecule B of (2).
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3. Supramolecular features
The packing of (1) and (2) is dominated by π–π interactions. In (1), the 13-membered rings related by a centre of inversion are stacked with a distance of 3.513 (2) Å between the centroids of two five-membered rings (symmetry operator: − x, − y, 1 − z). In (2), the six-membered ring C14A–C19A shows a short π–π interaction of 3.848 (3) Å with its inversion-related equivalent (symmetry operator: 2 − x, 1 − y, 1 − z). In addition, weak C—H⋯O and C—H⋯Br hydrogen bonds stabilize the crystal packing in (1) (see Table 2).
4. Database survey
Two similar structures have been published previously (Abu Thaher et al., 2016a,b). All crystal structures show the typical π–π interaction of the fused 13-membered ring system. The angles between the least-squares planes through the pyridine ring and the 13-membered ring vary from 50.38 (17) to 79.98 (7)°, probably depending on the molecular packing, while the angles between the substituted phenyl ring and the 13-membered ring range from 43.13 (15) to 78.64 (9)° depending on the size of the substituent.
5. Synthesis and crystallization
50.4 mg of NaH was added slowly to a solution of 399.4 mg of ethyl-2-benzimidazolcarboxylate in 30 ml dry THF and stirring continued at 298 K for 20 min. Then, 694 mg of N-(4-bromophenyl)-4-pyridinecarbohydrazonoyl chloride·HCl was added slowly in a portion-wise manner; in parallel 0.5 ml of Et3N was added dropwise. The reaction was stirred overnight (about 12 h); the reaction mixture was filtered and concentrated under vacuum. The solid residue was purified by (SiO2, heptane:ethyl acetate; 2:1, then 1:1). Suitable crystals for X-ray were obtained by slow evaporation of heptane/ethyl acetate (1:1).
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (Csp3 atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom). The s.o.f. for the chlorine atom in (1) was initially refined and then fixed at 0.125.
details are summarized in Table 3Supporting information
https://doi.org/10.1107/S2056989017011732/bt6995sup1.cif
contains datablocks 1, 2, global. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989017011732/bt69951sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989017011732/bt69952sup3.hkl
Data collection: X-AREA (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). Cell
X-AREA (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). Data reduction: X-RED32 (Stoe & Cie 2006) for (1); SMART and SAINT (Bruker, 1997) for (2). For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).C20H12BrN5O·0.143C20H11BrClN5O | F(000) = 1696 |
Mr = 422.56 | Dx = 1.607 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 25.7608 (18) Å | Cell parameters from 9637 reflections |
b = 11.0507 (5) Å | θ = 2.0–28.2° |
c = 12.2709 (10) Å | µ = 2.39 mm−1 |
β = 90.955 (6)° | T = 193 K |
V = 3492.7 (4) Å3 | Needle, colourless |
Z = 8 | 0.28 × 0.26 × 0.12 mm |
Stoe IPDS 2T diffractometer | 4317 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2369 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.041 |
rotation method scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: integration (X-RED32; Stoe & Cie 2006) | h = −34→34 |
Tmin = 0.488, Tmax = 0.744 | k = −14→14 |
11699 measured reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0663P)2 + 0.855P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4317 reflections | Δρmax = 0.65 e Å−3 |
253 parameters | Δρmin = −0.69 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | −0.02345 (2) | 0.15248 (4) | 0.54904 (4) | 0.06608 (19) | |
N1 | 0.11796 (12) | 0.5865 (3) | 0.4925 (2) | 0.0379 (7) | |
C2 | 0.14764 (14) | 0.6114 (4) | 0.4030 (3) | 0.0390 (8) | |
C3 | 0.17585 (14) | 0.7263 (4) | 0.4112 (3) | 0.0399 (8) | |
N4 | 0.20640 (12) | 0.7717 (3) | 0.3376 (3) | 0.0467 (8) | |
C5 | 0.22548 (14) | 0.8765 (4) | 0.3860 (3) | 0.0448 (9) | |
C6 | 0.25926 (16) | 0.9629 (5) | 0.3428 (4) | 0.0548 (11) | |
H6 | 0.2727 | 0.9540 | 0.2717 | 0.066* | |
C7 | 0.27228 (16) | 1.0608 (5) | 0.4064 (4) | 0.0580 (12) | |
H7 | 0.2945 | 1.1213 | 0.3779 | 0.070* | |
C8 | 0.25371 (17) | 1.0735 (4) | 0.5117 (4) | 0.0558 (11) | |
H8 | 0.2642 | 1.1420 | 0.5534 | 0.067* | |
C9 | 0.22053 (15) | 0.9903 (4) | 0.5579 (3) | 0.0483 (10) | |
H9 | 0.2084 | 0.9987 | 0.6302 | 0.058* | |
C10 | 0.20604 (14) | 0.8931 (4) | 0.4914 (3) | 0.0421 (9) | |
N11 | 0.17314 (11) | 0.7939 (3) | 0.5062 (2) | 0.0366 (7) | |
C12 | 0.14121 (14) | 0.7566 (3) | 0.5906 (3) | 0.0361 (8) | |
N13 | 0.11540 (11) | 0.6577 (3) | 0.5851 (2) | 0.0374 (6) | |
C14 | 0.08654 (14) | 0.4794 (3) | 0.5007 (3) | 0.0385 (8) | |
C15 | 0.08749 (17) | 0.4173 (4) | 0.5986 (3) | 0.0481 (9) | |
H15 | 0.1104 | 0.4414 | 0.6560 | 0.058* | |
C16 | 0.05456 (17) | 0.3193 (4) | 0.6119 (4) | 0.0523 (10) | |
H16 | 0.0545 | 0.2761 | 0.6788 | 0.063* | |
C17 | 0.02186 (16) | 0.2848 (4) | 0.5275 (4) | 0.0485 (9) | |
C18 | 0.02157 (15) | 0.3456 (4) | 0.4294 (3) | 0.0467 (9) | |
H18 | −0.0009 | 0.3203 | 0.3717 | 0.056* | |
C19 | 0.05422 (15) | 0.4436 (4) | 0.4156 (3) | 0.0441 (9) | |
H19 | 0.0544 | 0.4860 | 0.3483 | 0.053* | 0.875 |
O20 | 0.15031 (10) | 0.5434 (3) | 0.3248 (2) | 0.0490 (7) | |
Cl1 | 0.0394 (3) | 0.5181 (8) | 0.3084 (6) | 0.0457 (17) | 0.125 |
C21 | 0.13313 (13) | 0.8320 (3) | 0.6879 (3) | 0.0366 (8) | |
C22 | 0.11511 (16) | 0.9496 (4) | 0.6782 (3) | 0.0461 (9) | |
H22 | 0.1102 | 0.9862 | 0.6088 | 0.055* | |
C23 | 0.10454 (18) | 1.0123 (4) | 0.7731 (4) | 0.0550 (11) | |
H23 | 0.0923 | 1.0931 | 0.7663 | 0.066* | |
N24 | 0.11042 (14) | 0.9671 (3) | 0.8731 (3) | 0.0533 (9) | |
C25 | 0.12787 (16) | 0.8544 (4) | 0.8800 (3) | 0.0479 (9) | |
H25 | 0.1328 | 0.8206 | 0.9506 | 0.057* | |
C26 | 0.13934 (14) | 0.7828 (3) | 0.7911 (3) | 0.0414 (8) | |
H26 | 0.1512 | 0.7020 | 0.8006 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0666 (3) | 0.0435 (2) | 0.0878 (4) | −0.0127 (2) | −0.0093 (2) | 0.0036 (2) |
N1 | 0.0417 (16) | 0.0385 (16) | 0.0337 (15) | 0.0010 (14) | 0.0011 (13) | −0.0041 (13) |
C2 | 0.0370 (19) | 0.051 (2) | 0.0291 (18) | 0.0038 (17) | 0.0010 (14) | −0.0004 (16) |
C3 | 0.0360 (18) | 0.051 (2) | 0.0334 (18) | 0.0052 (17) | 0.0037 (15) | 0.0040 (16) |
N4 | 0.0416 (17) | 0.059 (2) | 0.0402 (17) | 0.0040 (16) | 0.0064 (14) | 0.0069 (16) |
C5 | 0.0339 (18) | 0.060 (3) | 0.040 (2) | 0.0046 (18) | 0.0047 (15) | 0.0128 (18) |
C6 | 0.042 (2) | 0.072 (3) | 0.051 (2) | 0.000 (2) | 0.0030 (18) | 0.023 (2) |
C7 | 0.043 (2) | 0.066 (3) | 0.066 (3) | −0.008 (2) | −0.001 (2) | 0.029 (2) |
C8 | 0.049 (2) | 0.056 (3) | 0.063 (3) | −0.013 (2) | −0.006 (2) | 0.015 (2) |
C9 | 0.044 (2) | 0.054 (2) | 0.047 (2) | −0.0078 (19) | −0.0043 (17) | 0.0080 (19) |
C10 | 0.0340 (18) | 0.046 (2) | 0.047 (2) | 0.0005 (16) | 0.0012 (16) | 0.0134 (17) |
N11 | 0.0346 (15) | 0.0443 (17) | 0.0309 (14) | −0.0018 (14) | 0.0033 (12) | 0.0035 (13) |
C12 | 0.0374 (18) | 0.0374 (19) | 0.0336 (18) | 0.0012 (16) | 0.0028 (14) | 0.0028 (15) |
N13 | 0.0421 (16) | 0.0377 (16) | 0.0325 (14) | 0.0008 (15) | 0.0029 (12) | −0.0019 (13) |
C14 | 0.0402 (19) | 0.0352 (18) | 0.0401 (19) | 0.0040 (16) | 0.0012 (15) | −0.0012 (15) |
C15 | 0.056 (2) | 0.047 (2) | 0.041 (2) | −0.0043 (19) | −0.0080 (18) | 0.0052 (17) |
C16 | 0.061 (3) | 0.045 (2) | 0.051 (2) | −0.006 (2) | −0.007 (2) | 0.0074 (18) |
C17 | 0.045 (2) | 0.038 (2) | 0.063 (3) | 0.0010 (18) | 0.0004 (19) | −0.0059 (19) |
C18 | 0.042 (2) | 0.048 (2) | 0.050 (2) | −0.0033 (19) | −0.0043 (17) | −0.0087 (19) |
C19 | 0.044 (2) | 0.048 (2) | 0.0399 (19) | 0.0084 (18) | −0.0026 (16) | −0.0065 (17) |
O20 | 0.0469 (15) | 0.0637 (18) | 0.0365 (13) | −0.0008 (14) | 0.0049 (12) | −0.0113 (13) |
Cl1 | 0.044 (4) | 0.055 (5) | 0.038 (4) | 0.007 (3) | 0.000 (3) | 0.008 (3) |
C21 | 0.0357 (17) | 0.0354 (19) | 0.0387 (18) | −0.0030 (15) | 0.0029 (14) | −0.0012 (15) |
C22 | 0.057 (2) | 0.038 (2) | 0.044 (2) | 0.0027 (18) | −0.0002 (18) | −0.0005 (16) |
C23 | 0.066 (3) | 0.038 (2) | 0.061 (3) | 0.003 (2) | −0.002 (2) | −0.0052 (19) |
N24 | 0.055 (2) | 0.050 (2) | 0.054 (2) | −0.0016 (17) | 0.0052 (17) | −0.0159 (17) |
C25 | 0.051 (2) | 0.049 (2) | 0.043 (2) | −0.006 (2) | 0.0061 (17) | −0.0021 (19) |
C26 | 0.045 (2) | 0.040 (2) | 0.0388 (19) | 0.0022 (17) | 0.0018 (16) | −0.0001 (16) |
Br1—C17 | 1.892 (4) | C14—C19 | 1.381 (5) |
N1—C2 | 1.377 (4) | C14—C15 | 1.384 (5) |
N1—N13 | 1.384 (4) | C15—C16 | 1.387 (6) |
N1—C14 | 1.439 (5) | C15—H15 | 0.9500 |
C2—O20 | 1.221 (4) | C16—C17 | 1.378 (6) |
C2—C3 | 1.465 (5) | C16—H16 | 0.9500 |
C3—N4 | 1.308 (4) | C17—C18 | 1.377 (6) |
C3—N11 | 1.388 (5) | C18—C19 | 1.384 (6) |
N4—C5 | 1.387 (5) | C18—H18 | 0.9500 |
C5—C6 | 1.401 (6) | C19—Cl1 | 1.593 (8) |
C5—C10 | 1.407 (5) | C19—H19 | 0.9500 |
C6—C7 | 1.372 (7) | Cl1—Cl1i | 2.467 (15) |
C6—H6 | 0.9500 | C21—C22 | 1.384 (5) |
C7—C8 | 1.392 (7) | C21—C26 | 1.385 (5) |
C7—H7 | 0.9500 | C22—C23 | 1.386 (6) |
C8—C9 | 1.384 (6) | C22—H22 | 0.9500 |
C8—H8 | 0.9500 | C23—N24 | 1.331 (6) |
C9—C10 | 1.396 (6) | C23—H23 | 0.9500 |
C9—H9 | 0.9500 | N24—C25 | 1.327 (5) |
C10—N11 | 1.399 (5) | C25—C26 | 1.383 (5) |
N11—C12 | 1.395 (4) | C25—H25 | 0.9500 |
C12—N13 | 1.281 (5) | C26—H26 | 0.9500 |
C12—C21 | 1.474 (5) | ||
C2—N1—N13 | 125.2 (3) | C19—C14—N1 | 121.0 (3) |
C2—N1—C14 | 122.7 (3) | C15—C14—N1 | 117.8 (3) |
N13—N1—C14 | 112.1 (3) | C14—C15—C16 | 119.2 (4) |
O20—C2—N1 | 122.9 (4) | C14—C15—H15 | 120.4 |
O20—C2—C3 | 123.6 (3) | C16—C15—H15 | 120.4 |
N1—C2—C3 | 113.6 (3) | C17—C16—C15 | 119.7 (4) |
N4—C3—N11 | 114.4 (4) | C17—C16—H16 | 120.2 |
N4—C3—C2 | 126.1 (3) | C15—C16—H16 | 120.2 |
N11—C3—C2 | 119.5 (3) | C18—C17—C16 | 121.1 (4) |
C3—N4—C5 | 103.8 (3) | C18—C17—Br1 | 120.3 (3) |
N4—C5—C6 | 128.7 (4) | C16—C17—Br1 | 118.6 (3) |
N4—C5—C10 | 111.9 (3) | C17—C18—C19 | 119.6 (4) |
C6—C5—C10 | 119.4 (4) | C17—C18—H18 | 120.2 |
C7—C6—C5 | 118.0 (4) | C19—C18—H18 | 120.2 |
C7—C6—H6 | 121.0 | C14—C19—C18 | 119.4 (4) |
C5—C6—H6 | 121.0 | C14—C19—Cl1 | 127.5 (4) |
C6—C7—C8 | 121.5 (4) | C18—C19—Cl1 | 111.6 (4) |
C6—C7—H7 | 119.3 | C14—C19—H19 | 120.3 |
C8—C7—H7 | 119.3 | C18—C19—H19 | 120.3 |
C9—C8—C7 | 122.5 (5) | C19—Cl1—Cl1i | 131.6 (5) |
C9—C8—H8 | 118.7 | C22—C21—C26 | 118.7 (3) |
C7—C8—H8 | 118.7 | C22—C21—C12 | 120.9 (3) |
C8—C9—C10 | 115.6 (4) | C26—C21—C12 | 120.2 (3) |
C8—C9—H9 | 122.2 | C21—C22—C23 | 117.9 (4) |
C10—C9—H9 | 122.2 | C21—C22—H22 | 121.1 |
C9—C10—N11 | 133.1 (3) | C23—C22—H22 | 121.1 |
C9—C10—C5 | 122.8 (4) | N24—C23—C22 | 124.5 (4) |
N11—C10—C5 | 104.1 (3) | N24—C23—H23 | 117.8 |
C3—N11—C12 | 120.2 (3) | C22—C23—H23 | 117.8 |
C3—N11—C10 | 105.9 (3) | C25—N24—C23 | 116.4 (3) |
C12—N11—C10 | 133.9 (3) | N24—C25—C26 | 124.3 (4) |
N13—C12—N11 | 121.7 (3) | N24—C25—H25 | 117.9 |
N13—C12—C21 | 116.4 (3) | C26—C25—H25 | 117.9 |
N11—C12—C21 | 121.8 (3) | C25—C26—C21 | 118.3 (4) |
C12—N13—N1 | 119.7 (3) | C25—C26—H26 | 120.9 |
C19—C14—C15 | 121.0 (4) | C21—C26—H26 | 120.9 |
N13—N1—C2—O20 | 176.9 (3) | N11—C12—N13—N1 | −1.5 (5) |
C14—N1—C2—O20 | −1.5 (6) | C21—C12—N13—N1 | 175.2 (3) |
N13—N1—C2—C3 | −2.5 (5) | C2—N1—N13—C12 | 1.5 (5) |
C14—N1—C2—C3 | 179.0 (3) | C14—N1—N13—C12 | −179.9 (3) |
O20—C2—C3—N4 | 1.0 (6) | C2—N1—C14—C19 | −47.3 (5) |
N1—C2—C3—N4 | −179.5 (4) | N13—N1—C14—C19 | 134.1 (3) |
O20—C2—C3—N11 | −175.8 (4) | C2—N1—C14—C15 | 136.3 (4) |
N1—C2—C3—N11 | 3.7 (5) | N13—N1—C14—C15 | −42.3 (4) |
N11—C3—N4—C5 | 0.0 (4) | C19—C14—C15—C16 | −1.4 (6) |
C2—C3—N4—C5 | −176.9 (4) | N1—C14—C15—C16 | 174.9 (4) |
C3—N4—C5—C6 | −178.4 (4) | C14—C15—C16—C17 | 0.5 (6) |
C3—N4—C5—C10 | 0.5 (4) | C15—C16—C17—C18 | 0.5 (6) |
N4—C5—C6—C7 | 179.2 (4) | C15—C16—C17—Br1 | −178.9 (3) |
C10—C5—C6—C7 | 0.4 (6) | C16—C17—C18—C19 | −0.7 (6) |
C5—C6—C7—C8 | 1.5 (7) | Br1—C17—C18—C19 | 178.8 (3) |
C6—C7—C8—C9 | −1.2 (7) | C15—C14—C19—C18 | 1.3 (5) |
C7—C8—C9—C10 | −1.0 (6) | N1—C14—C19—C18 | −175.0 (3) |
C8—C9—C10—N11 | −178.3 (4) | C15—C14—C19—Cl1 | 166.3 (5) |
C8—C9—C10—C5 | 2.9 (6) | N1—C14—C19—Cl1 | −10.0 (6) |
N4—C5—C10—C9 | 178.3 (4) | C17—C18—C19—C14 | −0.2 (6) |
C6—C5—C10—C9 | −2.7 (6) | C17—C18—C19—Cl1 | −167.5 (4) |
N4—C5—C10—N11 | −0.8 (4) | C14—C19—Cl1—Cl1i | −150.2 (4) |
C6—C5—C10—N11 | 178.3 (3) | C18—C19—Cl1—Cl1i | 15.8 (7) |
N4—C3—N11—C12 | 178.9 (3) | N13—C12—C21—C22 | −120.9 (4) |
C2—C3—N11—C12 | −4.0 (5) | N11—C12—C21—C22 | 55.7 (5) |
N4—C3—N11—C10 | −0.5 (4) | N13—C12—C21—C26 | 53.6 (5) |
C2—C3—N11—C10 | 176.7 (3) | N11—C12—C21—C26 | −129.7 (4) |
C9—C10—N11—C3 | −178.2 (4) | C26—C21—C22—C23 | 0.4 (6) |
C5—C10—N11—C3 | 0.7 (4) | C12—C21—C22—C23 | 175.1 (4) |
C9—C10—N11—C12 | 2.6 (7) | C21—C22—C23—N24 | −0.2 (7) |
C5—C10—N11—C12 | −178.5 (4) | C22—C23—N24—C25 | 0.3 (7) |
C3—N11—C12—N13 | 2.9 (5) | C23—N24—C25—C26 | −0.8 (6) |
C10—N11—C12—N13 | −178.0 (4) | N24—C25—C26—C21 | 1.1 (6) |
C3—N11—C12—C21 | −173.6 (3) | C22—C21—C26—C25 | −0.9 (5) |
C10—N11—C12—C21 | 5.5 (6) | C12—C21—C26—C25 | −175.6 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O20ii | 0.95 | 2.53 | 3.258 (5) | 134 |
C15—H15···O20iii | 0.95 | 2.30 | 3.219 (5) | 162 |
C23—H23···Br1iv | 0.95 | 2.97 | 3.417 (4) | 110 |
Symmetry codes: (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, −y+1, z+1/2; (iv) −x, y+1, −z+3/2. |
C20H11BrClN5O | F(000) = 1808 |
Mr = 452.70 | Dx = 1.619 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1074 (7) Å | Cell parameters from 1476 reflections |
b = 32.754 (3) Å | θ = 2.5–19.7° |
c = 16.1505 (15) Å | µ = 2.38 mm−1 |
β = 98.914 (3)° | T = 173 K |
V = 3714.4 (6) Å3 | Column, colourless |
Z = 8 | 0.28 × 0.03 × 0.02 mm |
Bruker SMART APEXII diffractometer | 3614 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.152 |
CCD scan | θmax = 27.8°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.872, Tmax = 0.947 | k = −41→42 |
31679 measured reflections | l = −21→21 |
8805 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.012P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.72 | (Δ/σ)max = 0.001 |
8805 reflections | Δρmax = 0.42 e Å−3 |
505 parameters | Δρmin = −0.49 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1A | 0.96493 (8) | 0.44476 (2) | 0.31444 (3) | 0.04310 (17) | |
Cl1A | 1.36103 (18) | 0.46317 (5) | 0.63345 (8) | 0.0432 (4) | |
N1A | 0.9964 (5) | 0.43502 (10) | 0.6924 (2) | 0.0173 (9) | |
C2A | 1.0976 (6) | 0.40286 (13) | 0.7334 (3) | 0.0176 (11) | |
C3A | 1.0808 (6) | 0.40069 (13) | 0.8227 (3) | 0.0165 (11) | |
N4A | 1.1804 (5) | 0.37751 (11) | 0.8789 (2) | 0.0208 (9) | |
C5A | 1.1249 (6) | 0.38977 (13) | 0.9538 (3) | 0.0170 (11) | |
C6A | 1.1926 (6) | 0.37608 (14) | 1.0348 (3) | 0.0236 (12) | |
H6A | 1.2828 | 0.3545 | 1.0443 | 0.028* | |
C7A | 1.1243 (6) | 0.39487 (15) | 1.1007 (3) | 0.0276 (12) | |
H7A | 1.1682 | 0.3861 | 1.1564 | 0.033* | |
C8A | 0.9922 (6) | 0.42647 (14) | 1.0869 (3) | 0.0260 (12) | |
H8A | 0.9478 | 0.4387 | 1.1336 | 0.031* | |
C9A | 0.9232 (6) | 0.44073 (14) | 1.0073 (3) | 0.0244 (12) | |
H9A | 0.8356 | 0.4628 | 0.9984 | 0.029* | |
C10A | 0.9887 (6) | 0.42112 (13) | 0.9411 (3) | 0.0173 (11) | |
N11A | 0.9589 (5) | 0.42773 (10) | 0.8541 (2) | 0.0155 (9) | |
C12A | 0.8362 (6) | 0.45263 (13) | 0.8002 (3) | 0.0148 (10) | |
N13A | 0.8534 (5) | 0.45672 (10) | 0.7225 (2) | 0.0180 (9) | |
C14A | 0.9909 (6) | 0.43961 (13) | 0.6034 (3) | 0.0179 (11) | |
C15A | 0.8217 (7) | 0.43142 (14) | 0.5505 (3) | 0.0256 (12) | |
H15A | 0.7111 | 0.4242 | 0.5735 | 0.031* | |
C16A | 0.8132 (7) | 0.43367 (13) | 0.4648 (3) | 0.0236 (12) | |
H16A | 0.6973 | 0.4281 | 0.4287 | 0.028* | |
C17A | 0.9736 (7) | 0.44400 (15) | 0.4324 (3) | 0.0257 (12) | |
C18A | 1.1435 (7) | 0.45322 (14) | 0.4828 (3) | 0.0260 (12) | |
H18A | 1.2525 | 0.4611 | 0.4593 | 0.031* | |
C19A | 1.1500 (6) | 0.45062 (14) | 0.5696 (3) | 0.0218 (11) | |
O20A | 1.1978 (4) | 0.38045 (9) | 0.69899 (18) | 0.0270 (8) | |
C21A | 0.6743 (6) | 0.47361 (13) | 0.8297 (3) | 0.0148 (10) | |
C22A | 0.5556 (6) | 0.45303 (14) | 0.8762 (3) | 0.0210 (11) | |
H22A | 0.5774 | 0.4252 | 0.8909 | 0.025* | |
C23A | 0.4048 (6) | 0.47409 (15) | 0.9007 (3) | 0.0252 (12) | |
H23A | 0.3270 | 0.4600 | 0.9342 | 0.030* | |
N24A | 0.3612 (5) | 0.51258 (13) | 0.8807 (2) | 0.0304 (11) | |
C25A | 0.4749 (7) | 0.53165 (15) | 0.8346 (3) | 0.0297 (13) | |
H25A | 0.4465 | 0.5592 | 0.8189 | 0.036* | |
C26A | 0.6319 (6) | 0.51357 (14) | 0.8083 (3) | 0.0241 (12) | |
H26A | 0.7091 | 0.5286 | 0.7760 | 0.029* | |
Br1B | 0.47931 (8) | 0.36336 (2) | 0.29334 (3) | 0.03770 (16) | |
Cl1B | 0.84923 (18) | 0.30274 (4) | 0.59237 (8) | 0.0411 (4) | |
N1B | 0.4871 (5) | 0.32230 (11) | 0.6617 (2) | 0.0166 (9) | |
C2B | 0.5946 (6) | 0.34732 (14) | 0.7198 (3) | 0.0196 (11) | |
C3B | 0.5793 (6) | 0.33619 (14) | 0.8071 (3) | 0.0201 (11) | |
N4B | 0.6815 (5) | 0.35077 (11) | 0.8745 (2) | 0.0201 (9) | |
C5B | 0.6216 (6) | 0.32841 (14) | 0.9391 (3) | 0.0197 (11) | |
C6B | 0.6875 (7) | 0.33113 (15) | 1.0247 (3) | 0.0277 (12) | |
H6B | 0.7827 | 0.3504 | 1.0461 | 0.033* | |
C7B | 0.6107 (7) | 0.30507 (15) | 1.0773 (3) | 0.0303 (13) | |
H7B | 0.6537 | 0.3064 | 1.1359 | 0.036* | |
C8B | 0.4708 (7) | 0.27673 (14) | 1.0461 (3) | 0.0263 (12) | |
H8B | 0.4211 | 0.2592 | 1.0842 | 0.032* | |
C9B | 0.4024 (6) | 0.27336 (14) | 0.9619 (3) | 0.0220 (11) | |
H9B | 0.3088 | 0.2537 | 0.9410 | 0.026* | |
C10B | 0.4779 (6) | 0.30041 (14) | 0.9083 (3) | 0.0200 (11) | |
N11B | 0.4492 (5) | 0.30633 (10) | 0.8217 (2) | 0.0155 (8) | |
C12B | 0.3257 (6) | 0.28919 (13) | 0.7551 (3) | 0.0170 (11) | |
N13B | 0.3423 (5) | 0.29650 (11) | 0.6775 (2) | 0.0189 (9) | |
C14B | 0.4850 (6) | 0.33054 (13) | 0.5739 (3) | 0.0160 (10) | |
C15B | 0.3200 (6) | 0.34514 (13) | 0.5259 (3) | 0.0225 (12) | |
H15B | 0.2088 | 0.3488 | 0.5511 | 0.027* | |
C16B | 0.3145 (7) | 0.35454 (14) | 0.4419 (3) | 0.0277 (12) | |
H16B | 0.2020 | 0.3650 | 0.4092 | 0.033* | |
C17B | 0.4782 (7) | 0.34825 (14) | 0.4070 (3) | 0.0222 (11) | |
C18B | 0.6421 (6) | 0.33246 (13) | 0.4522 (3) | 0.0216 (11) | |
H18B | 0.7513 | 0.3278 | 0.4263 | 0.026* | |
C19B | 0.6451 (6) | 0.32348 (13) | 0.5359 (3) | 0.0185 (11) | |
O20B | 0.6995 (4) | 0.37385 (9) | 0.70109 (18) | 0.0276 (8) | |
C21B | 0.1679 (6) | 0.26314 (14) | 0.7722 (3) | 0.0195 (11) | |
C22B | 0.0357 (6) | 0.27684 (15) | 0.8214 (3) | 0.0271 (12) | |
H22B | 0.0425 | 0.3036 | 0.8443 | 0.033* | |
C23B | −0.1051 (7) | 0.24998 (16) | 0.8354 (3) | 0.0347 (14) | |
H23B | −0.1953 | 0.2596 | 0.8685 | 0.042* | |
N24B | −0.1270 (6) | 0.21199 (13) | 0.8073 (3) | 0.0349 (11) | |
C25B | −0.0011 (7) | 0.19985 (15) | 0.7593 (3) | 0.0365 (14) | |
H25B | −0.0126 | 0.1730 | 0.7369 | 0.044* | |
C26B | 0.1469 (6) | 0.22436 (14) | 0.7400 (3) | 0.0271 (12) | |
H26B | 0.2322 | 0.2143 | 0.7050 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1A | 0.0516 (4) | 0.0607 (4) | 0.0186 (3) | −0.0114 (3) | 0.0105 (3) | 0.0025 (3) |
Cl1A | 0.0284 (8) | 0.0656 (11) | 0.0359 (8) | −0.0056 (7) | 0.0059 (7) | 0.0006 (7) |
N1A | 0.018 (2) | 0.020 (2) | 0.016 (2) | 0.0015 (18) | 0.0088 (17) | 0.0006 (16) |
C2A | 0.018 (3) | 0.015 (3) | 0.021 (3) | 0.001 (2) | 0.003 (2) | 0.001 (2) |
C3A | 0.016 (2) | 0.018 (3) | 0.016 (3) | −0.002 (2) | 0.003 (2) | −0.004 (2) |
N4A | 0.020 (2) | 0.026 (3) | 0.017 (2) | 0.0050 (19) | 0.0047 (18) | −0.0014 (17) |
C5A | 0.014 (2) | 0.019 (3) | 0.017 (3) | 0.002 (2) | 0.001 (2) | 0.002 (2) |
C6A | 0.016 (3) | 0.027 (3) | 0.027 (3) | 0.006 (2) | 0.003 (2) | 0.003 (2) |
C7A | 0.024 (3) | 0.041 (4) | 0.017 (3) | 0.006 (3) | −0.002 (2) | 0.006 (2) |
C8A | 0.024 (3) | 0.034 (3) | 0.021 (3) | 0.002 (2) | 0.008 (2) | −0.005 (2) |
C9A | 0.017 (3) | 0.033 (3) | 0.023 (3) | 0.003 (2) | 0.003 (2) | 0.001 (2) |
C10A | 0.019 (3) | 0.020 (3) | 0.013 (2) | −0.002 (2) | 0.004 (2) | 0.001 (2) |
N11A | 0.013 (2) | 0.019 (2) | 0.016 (2) | 0.0031 (17) | 0.0055 (17) | −0.0021 (16) |
C12A | 0.009 (2) | 0.014 (3) | 0.021 (3) | 0.002 (2) | 0.002 (2) | −0.002 (2) |
N13A | 0.017 (2) | 0.018 (2) | 0.020 (2) | 0.0024 (18) | 0.0047 (18) | 0.0010 (17) |
C14A | 0.018 (3) | 0.016 (3) | 0.020 (3) | 0.002 (2) | 0.006 (2) | 0.000 (2) |
C15A | 0.023 (3) | 0.032 (3) | 0.024 (3) | −0.006 (2) | 0.010 (2) | 0.003 (2) |
C16A | 0.024 (3) | 0.023 (3) | 0.021 (3) | −0.004 (2) | −0.006 (2) | 0.000 (2) |
C17A | 0.033 (3) | 0.031 (3) | 0.015 (2) | −0.002 (3) | 0.012 (2) | 0.001 (2) |
C18A | 0.026 (3) | 0.029 (3) | 0.027 (3) | −0.001 (2) | 0.016 (2) | 0.004 (2) |
C19A | 0.014 (3) | 0.027 (3) | 0.024 (3) | −0.003 (2) | 0.000 (2) | −0.006 (2) |
O20A | 0.031 (2) | 0.029 (2) | 0.0237 (19) | 0.0132 (16) | 0.0131 (16) | −0.0014 (15) |
C21A | 0.013 (2) | 0.017 (3) | 0.013 (2) | 0.002 (2) | −0.004 (2) | −0.0012 (19) |
C22A | 0.018 (3) | 0.021 (3) | 0.025 (3) | 0.000 (2) | 0.008 (2) | 0.000 (2) |
C23A | 0.016 (3) | 0.028 (3) | 0.033 (3) | 0.001 (2) | 0.010 (2) | 0.002 (2) |
N24A | 0.024 (2) | 0.031 (3) | 0.040 (3) | 0.008 (2) | 0.015 (2) | −0.001 (2) |
C25A | 0.033 (3) | 0.017 (3) | 0.041 (3) | 0.004 (2) | 0.012 (3) | 0.003 (2) |
C26A | 0.016 (3) | 0.028 (3) | 0.030 (3) | 0.000 (2) | 0.006 (2) | 0.000 (2) |
Br1B | 0.0445 (4) | 0.0483 (4) | 0.0207 (3) | 0.0002 (3) | 0.0061 (3) | 0.0076 (3) |
Cl1B | 0.0281 (8) | 0.0597 (11) | 0.0365 (8) | 0.0102 (7) | 0.0084 (6) | 0.0071 (7) |
N1B | 0.017 (2) | 0.017 (2) | 0.017 (2) | −0.0045 (18) | 0.0068 (18) | 0.0012 (17) |
C2B | 0.014 (3) | 0.026 (3) | 0.019 (3) | 0.003 (2) | 0.005 (2) | −0.002 (2) |
C3B | 0.020 (3) | 0.020 (3) | 0.022 (3) | −0.005 (2) | 0.010 (2) | −0.002 (2) |
N4B | 0.021 (2) | 0.021 (2) | 0.018 (2) | −0.0038 (18) | 0.0020 (18) | 0.0006 (17) |
C5B | 0.018 (3) | 0.022 (3) | 0.018 (3) | 0.005 (2) | −0.001 (2) | 0.001 (2) |
C6B | 0.023 (3) | 0.034 (3) | 0.026 (3) | −0.001 (2) | 0.001 (2) | −0.007 (2) |
C7B | 0.034 (3) | 0.042 (4) | 0.012 (3) | 0.007 (3) | −0.004 (2) | 0.003 (2) |
C8B | 0.031 (3) | 0.026 (3) | 0.026 (3) | 0.005 (3) | 0.018 (2) | 0.008 (2) |
C9B | 0.028 (3) | 0.020 (3) | 0.020 (3) | −0.001 (2) | 0.009 (2) | 0.002 (2) |
C10B | 0.022 (3) | 0.022 (3) | 0.017 (3) | 0.005 (2) | 0.004 (2) | 0.003 (2) |
N11B | 0.015 (2) | 0.019 (2) | 0.013 (2) | −0.0006 (18) | 0.0045 (17) | −0.0005 (17) |
C12B | 0.011 (2) | 0.021 (3) | 0.019 (3) | 0.001 (2) | 0.003 (2) | 0.000 (2) |
N13B | 0.017 (2) | 0.020 (2) | 0.021 (2) | −0.0023 (18) | 0.0067 (18) | −0.0003 (17) |
C14B | 0.020 (3) | 0.015 (3) | 0.015 (2) | 0.001 (2) | 0.006 (2) | −0.0019 (19) |
C15B | 0.013 (3) | 0.031 (3) | 0.025 (3) | 0.005 (2) | 0.008 (2) | −0.001 (2) |
C16B | 0.022 (3) | 0.036 (3) | 0.025 (3) | 0.007 (2) | 0.002 (2) | 0.002 (2) |
C17B | 0.031 (3) | 0.021 (3) | 0.015 (3) | −0.002 (2) | 0.008 (2) | 0.002 (2) |
C18B | 0.018 (3) | 0.028 (3) | 0.019 (3) | 0.000 (2) | 0.007 (2) | 0.000 (2) |
C19B | 0.018 (3) | 0.018 (3) | 0.020 (3) | 0.004 (2) | 0.004 (2) | 0.003 (2) |
O20B | 0.030 (2) | 0.030 (2) | 0.0238 (19) | −0.0150 (17) | 0.0078 (16) | 0.0011 (15) |
C21B | 0.021 (3) | 0.017 (3) | 0.020 (3) | −0.005 (2) | 0.003 (2) | 0.001 (2) |
C22B | 0.026 (3) | 0.027 (3) | 0.030 (3) | 0.001 (2) | 0.011 (2) | −0.003 (2) |
C23B | 0.021 (3) | 0.042 (4) | 0.044 (4) | 0.002 (3) | 0.015 (3) | 0.003 (3) |
N24B | 0.027 (3) | 0.037 (3) | 0.043 (3) | −0.007 (2) | 0.013 (2) | 0.000 (2) |
C25B | 0.045 (4) | 0.023 (3) | 0.043 (4) | −0.008 (3) | 0.015 (3) | −0.011 (3) |
C26B | 0.026 (3) | 0.029 (3) | 0.029 (3) | −0.005 (3) | 0.013 (2) | −0.001 (2) |
Br1A—C17A | 1.896 (4) | Br1B—C17B | 1.902 (4) |
Cl1A—C19A | 1.733 (4) | Cl1B—C19B | 1.729 (4) |
N1A—C2A | 1.385 (5) | N1B—C2B | 1.383 (5) |
N1A—N13A | 1.389 (4) | N1B—N13B | 1.385 (4) |
N1A—C14A | 1.439 (5) | N1B—C14B | 1.442 (5) |
C2A—O20A | 1.215 (5) | C2B—O20B | 1.213 (5) |
C2A—C3A | 1.467 (6) | C2B—C3B | 1.476 (6) |
C3A—N4A | 1.305 (5) | C3B—N4B | 1.302 (5) |
C3A—N11A | 1.389 (5) | C3B—N11B | 1.391 (5) |
N4A—C5A | 1.389 (5) | N4B—C5B | 1.394 (5) |
C5A—C6A | 1.396 (6) | C5B—C6B | 1.391 (6) |
C5A—C10A | 1.404 (6) | C5B—C10B | 1.405 (6) |
C6A—C7A | 1.381 (6) | C6B—C7B | 1.375 (6) |
C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
C7A—C8A | 1.392 (6) | C7B—C8B | 1.396 (6) |
C7A—H7A | 0.9500 | C7B—H7B | 0.9500 |
C8A—C9A | 1.384 (6) | C8B—C9B | 1.376 (6) |
C8A—H8A | 0.9500 | C8B—H8B | 0.9500 |
C9A—C10A | 1.387 (6) | C9B—C10B | 1.402 (6) |
C9A—H9A | 0.9500 | C9B—H9B | 0.9500 |
C10A—N11A | 1.405 (5) | C10B—N11B | 1.395 (5) |
N11A—C12A | 1.396 (5) | N11B—C12B | 1.397 (5) |
C12A—N13A | 1.285 (5) | C12B—N13B | 1.299 (5) |
C12A—C21A | 1.482 (5) | C12B—C21B | 1.469 (6) |
C14A—C19A | 1.378 (6) | C14B—C15B | 1.386 (6) |
C14A—C15A | 1.390 (6) | C14B—C19B | 1.393 (5) |
C15A—C16A | 1.377 (6) | C15B—C16B | 1.387 (6) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.369 (6) | C16B—C17B | 1.385 (6) |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.382 (6) | C17B—C18B | 1.376 (6) |
C18A—C19A | 1.397 (6) | C18B—C19B | 1.380 (5) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C21A—C26A | 1.375 (6) | C21B—C26B | 1.372 (6) |
C21A—C22A | 1.388 (5) | C21B—C22B | 1.395 (6) |
C22A—C23A | 1.383 (6) | C22B—C23B | 1.377 (6) |
C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
C23A—N24A | 1.326 (5) | C23B—N24B | 1.326 (6) |
C23A—H23A | 0.9500 | C23B—H23B | 0.9500 |
N24A—C25A | 1.336 (5) | N24B—C25B | 1.332 (6) |
C25A—C26A | 1.387 (6) | C25B—C26B | 1.396 (6) |
C25A—H25A | 0.9500 | C25B—H25B | 0.9500 |
C26A—H26A | 0.9500 | C26B—H26B | 0.9500 |
C2A—N1A—N13A | 125.1 (3) | C2B—N1B—N13B | 125.8 (3) |
C2A—N1A—C14A | 119.2 (3) | C2B—N1B—C14B | 118.5 (4) |
N13A—N1A—C14A | 112.9 (3) | N13B—N1B—C14B | 113.6 (3) |
O20A—C2A—N1A | 122.6 (4) | O20B—C2B—N1B | 123.5 (4) |
O20A—C2A—C3A | 124.2 (4) | O20B—C2B—C3B | 123.6 (4) |
N1A—C2A—C3A | 113.0 (4) | N1B—C2B—C3B | 112.8 (4) |
N4A—C3A—N11A | 114.8 (4) | N4B—C3B—N11B | 114.5 (4) |
N4A—C3A—C2A | 126.5 (4) | N4B—C3B—C2B | 126.4 (4) |
N11A—C3A—C2A | 118.6 (4) | N11B—C3B—C2B | 119.0 (4) |
C3A—N4A—C5A | 104.0 (4) | C3B—N4B—C5B | 103.7 (4) |
N4A—C5A—C6A | 128.3 (4) | C6B—C5B—N4B | 127.9 (4) |
N4A—C5A—C10A | 111.5 (4) | C6B—C5B—C10B | 120.5 (4) |
C6A—C5A—C10A | 120.1 (4) | N4B—C5B—C10B | 111.6 (4) |
C7A—C6A—C5A | 117.9 (4) | C7B—C6B—C5B | 117.9 (4) |
C7A—C6A—H6A | 121.1 | C7B—C6B—H6B | 121.0 |
C5A—C6A—H6A | 121.1 | C5B—C6B—H6B | 121.0 |
C6A—C7A—C8A | 121.1 (4) | C6B—C7B—C8B | 121.2 (4) |
C6A—C7A—H7A | 119.5 | C6B—C7B—H7B | 119.4 |
C8A—C7A—H7A | 119.5 | C8B—C7B—H7B | 119.4 |
C9A—C8A—C7A | 122.2 (4) | C9B—C8B—C7B | 122.2 (4) |
C9A—C8A—H8A | 118.9 | C9B—C8B—H8B | 118.9 |
C7A—C8A—H8A | 118.9 | C7B—C8B—H8B | 118.9 |
C8A—C9A—C10A | 116.5 (4) | C8B—C9B—C10B | 116.7 (4) |
C8A—C9A—H9A | 121.7 | C8B—C9B—H9B | 121.7 |
C10A—C9A—H9A | 121.7 | C10B—C9B—H9B | 121.7 |
C9A—C10A—C5A | 122.2 (4) | N11B—C10B—C9B | 134.1 (4) |
C9A—C10A—N11A | 133.0 (4) | N11B—C10B—C5B | 104.5 (4) |
C5A—C10A—N11A | 104.6 (4) | C9B—C10B—C5B | 121.4 (4) |
C3A—N11A—C12A | 120.6 (4) | C3B—N11B—C10B | 105.7 (4) |
C3A—N11A—C10A | 105.1 (3) | C3B—N11B—C12B | 120.5 (4) |
C12A—N11A—C10A | 134.2 (4) | C10B—N11B—C12B | 133.9 (4) |
N13A—C12A—N11A | 121.6 (4) | N13B—C12B—N11B | 121.9 (4) |
N13A—C12A—C21A | 117.5 (4) | N13B—C12B—C21B | 118.3 (4) |
N11A—C12A—C21A | 120.8 (4) | N11B—C12B—C21B | 119.7 (4) |
C12A—N13A—N1A | 118.3 (3) | C12B—N13B—N1B | 118.1 (4) |
C19A—C14A—C15A | 119.4 (4) | C15B—C14B—C19B | 119.3 (4) |
C19A—C14A—N1A | 121.7 (4) | C15B—C14B—N1B | 119.5 (4) |
C15A—C14A—N1A | 118.8 (4) | C19B—C14B—N1B | 121.1 (4) |
C16A—C15A—C14A | 120.5 (4) | C14B—C15B—C16B | 121.1 (4) |
C16A—C15A—H15A | 119.8 | C14B—C15B—H15B | 119.4 |
C14A—C15A—H15A | 119.8 | C16B—C15B—H15B | 119.4 |
C17A—C16A—C15A | 119.2 (4) | C17B—C16B—C15B | 117.9 (4) |
C17A—C16A—H16A | 120.4 | C17B—C16B—H16B | 121.1 |
C15A—C16A—H16A | 120.4 | C15B—C16B—H16B | 121.1 |
C16A—C17A—C18A | 122.1 (4) | C18B—C17B—C16B | 122.4 (4) |
C16A—C17A—Br1A | 119.3 (4) | C18B—C17B—Br1B | 118.7 (3) |
C18A—C17A—Br1A | 118.6 (3) | C16B—C17B—Br1B | 118.9 (4) |
C17A—C18A—C19A | 117.9 (4) | C17B—C18B—C19B | 118.9 (4) |
C17A—C18A—H18A | 121.0 | C17B—C18B—H18B | 120.5 |
C19A—C18A—H18A | 121.0 | C19B—C18B—H18B | 120.5 |
C14A—C19A—C18A | 120.8 (4) | C18B—C19B—C14B | 120.4 (4) |
C14A—C19A—Cl1A | 120.9 (3) | C18B—C19B—Cl1B | 119.0 (3) |
C18A—C19A—Cl1A | 118.3 (3) | C14B—C19B—Cl1B | 120.6 (3) |
C26A—C21A—C22A | 118.1 (4) | C26B—C21B—C22B | 118.0 (4) |
C26A—C21A—C12A | 120.7 (4) | C26B—C21B—C12B | 120.5 (4) |
C22A—C21A—C12A | 121.1 (4) | C22B—C21B—C12B | 121.4 (4) |
C23A—C22A—C21A | 118.4 (4) | C23B—C22B—C21B | 117.3 (5) |
C23A—C22A—H22A | 120.8 | C23B—C22B—H22B | 121.3 |
C21A—C22A—H22A | 120.8 | C21B—C22B—H22B | 121.3 |
N24A—C23A—C22A | 124.6 (4) | N24B—C23B—C22B | 126.3 (5) |
N24A—C23A—H23A | 117.7 | N24B—C23B—H23B | 116.8 |
C22A—C23A—H23A | 117.7 | C22B—C23B—H23B | 116.8 |
C23A—N24A—C25A | 116.2 (4) | C23B—N24B—C25B | 115.2 (4) |
N24A—C25A—C26A | 123.8 (5) | N24B—C25B—C26B | 123.7 (5) |
N24A—C25A—H25A | 118.1 | N24B—C25B—H25B | 118.1 |
C26A—C25A—H25A | 118.1 | C26B—C25B—H25B | 118.1 |
C21A—C26A—C25A | 119.0 (4) | C21B—C26B—C25B | 119.3 (4) |
C21A—C26A—H26A | 120.5 | C21B—C26B—H26B | 120.3 |
C25A—C26A—H26A | 120.5 | C25B—C26B—H26B | 120.3 |
N13A—N1A—C2A—O20A | 167.2 (4) | N13B—N1B—C2B—O20B | −168.4 (4) |
C14A—N1A—C2A—O20A | 7.3 (6) | C14B—N1B—C2B—O20B | −6.1 (6) |
N13A—N1A—C2A—C3A | −16.7 (6) | N13B—N1B—C2B—C3B | 16.1 (6) |
C14A—N1A—C2A—C3A | −176.5 (4) | C14B—N1B—C2B—C3B | 178.3 (4) |
O20A—C2A—C3A—N4A | 6.3 (8) | O20B—C2B—C3B—N4B | −4.7 (8) |
N1A—C2A—C3A—N4A | −169.7 (4) | N1B—C2B—C3B—N4B | 170.8 (4) |
O20A—C2A—C3A—N11A | −179.0 (4) | O20B—C2B—C3B—N11B | 177.6 (4) |
N1A—C2A—C3A—N11A | 4.9 (6) | N1B—C2B—C3B—N11B | −6.8 (6) |
N11A—C3A—N4A—C5A | −0.7 (5) | N11B—C3B—N4B—C5B | 2.0 (5) |
C2A—C3A—N4A—C5A | 174.1 (4) | C2B—C3B—N4B—C5B | −175.7 (4) |
C3A—N4A—C5A—C6A | −177.2 (5) | C3B—N4B—C5B—C6B | 178.7 (4) |
C3A—N4A—C5A—C10A | −0.1 (5) | C3B—N4B—C5B—C10B | −1.0 (5) |
N4A—C5A—C6A—C7A | 175.7 (4) | N4B—C5B—C6B—C7B | −178.2 (4) |
C10A—C5A—C6A—C7A | −1.3 (7) | C10B—C5B—C6B—C7B | 1.4 (7) |
C5A—C6A—C7A—C8A | 0.0 (7) | C5B—C6B—C7B—C8B | −0.1 (7) |
C6A—C7A—C8A—C9A | −0.2 (7) | C6B—C7B—C8B—C9B | −0.1 (7) |
C7A—C8A—C9A—C10A | 1.7 (7) | C7B—C8B—C9B—C10B | −1.1 (7) |
C8A—C9A—C10A—C5A | −3.0 (7) | C8B—C9B—C10B—N11B | 179.0 (4) |
C8A—C9A—C10A—N11A | −176.8 (4) | C8B—C9B—C10B—C5B | 2.4 (7) |
N4A—C5A—C10A—C9A | −174.5 (4) | C6B—C5B—C10B—N11B | 179.9 (4) |
C6A—C5A—C10A—C9A | 2.9 (7) | N4B—C5B—C10B—N11B | −0.4 (5) |
N4A—C5A—C10A—N11A | 0.8 (5) | C6B—C5B—C10B—C9B | −2.6 (7) |
C6A—C5A—C10A—N11A | 178.2 (4) | N4B—C5B—C10B—C9B | 177.0 (4) |
N4A—C3A—N11A—C12A | −176.3 (4) | N4B—C3B—N11B—C10B | −2.3 (5) |
C2A—C3A—N11A—C12A | 8.5 (6) | C2B—C3B—N11B—C10B | 175.6 (4) |
N4A—C3A—N11A—C10A | 1.2 (5) | N4B—C3B—N11B—C12B | 177.6 (4) |
C2A—C3A—N11A—C10A | −174.0 (4) | C2B—C3B—N11B—C12B | −4.5 (6) |
C9A—C10A—N11A—C3A | 173.4 (5) | C9B—C10B—N11B—C3B | −175.4 (5) |
C5A—C10A—N11A—C3A | −1.1 (4) | C5B—C10B—N11B—C3B | 1.5 (4) |
C9A—C10A—N11A—C12A | −9.6 (8) | C9B—C10B—N11B—C12B | 4.6 (8) |
C5A—C10A—N11A—C12A | 175.9 (4) | C5B—C10B—N11B—C12B | −178.4 (4) |
C3A—N11A—C12A—N13A | −12.1 (6) | C3B—N11B—C12B—N13B | 8.6 (6) |
C10A—N11A—C12A—N13A | 171.3 (4) | C10B—N11B—C12B—N13B | −171.5 (4) |
C3A—N11A—C12A—C21A | 164.6 (4) | C3B—N11B—C12B—C21B | −169.4 (4) |
C10A—N11A—C12A—C21A | −12.1 (7) | C10B—N11B—C12B—C21B | 10.5 (7) |
N11A—C12A—N13A—N1A | 1.2 (6) | N11B—C12B—N13B—N1B | −0.4 (6) |
C21A—C12A—N13A—N1A | −175.6 (4) | C21B—C12B—N13B—N1B | 177.7 (4) |
C2A—N1A—N13A—C12A | 14.2 (6) | C2B—N1B—N13B—C12B | −13.0 (6) |
C14A—N1A—N13A—C12A | 175.2 (4) | C14B—N1B—N13B—C12B | −176.0 (4) |
C2A—N1A—C14A—C19A | −69.0 (6) | C2B—N1B—C14B—C15B | −110.7 (5) |
N13A—N1A—C14A—C19A | 128.8 (4) | N13B—N1B—C14B—C15B | 53.7 (5) |
C2A—N1A—C14A—C15A | 108.9 (5) | C2B—N1B—C14B—C19B | 70.4 (5) |
N13A—N1A—C14A—C15A | −53.3 (5) | N13B—N1B—C14B—C19B | −125.3 (4) |
C19A—C14A—C15A—C16A | 1.0 (7) | C19B—C14B—C15B—C16B | −2.9 (7) |
N1A—C14A—C15A—C16A | −177.0 (4) | N1B—C14B—C15B—C16B | 178.1 (4) |
C14A—C15A—C16A—C17A | 0.1 (7) | C14B—C15B—C16B—C17B | 1.0 (7) |
C15A—C16A—C17A—C18A | −1.6 (7) | C15B—C16B—C17B—C18B | 1.3 (7) |
C15A—C16A—C17A—Br1A | 177.2 (3) | C15B—C16B—C17B—Br1B | −176.9 (3) |
C16A—C17A—C18A—C19A | 1.8 (7) | C16B—C17B—C18B—C19B | −1.6 (7) |
Br1A—C17A—C18A—C19A | −177.0 (3) | Br1B—C17B—C18B—C19B | 176.6 (3) |
C15A—C14A—C19A—C18A | −0.7 (7) | C17B—C18B—C19B—C14B | −0.4 (7) |
N1A—C14A—C19A—C18A | 177.3 (4) | C17B—C18B—C19B—Cl1B | 178.8 (3) |
C15A—C14A—C19A—Cl1A | 177.3 (3) | C15B—C14B—C19B—C18B | 2.6 (7) |
N1A—C14A—C19A—Cl1A | −4.8 (6) | N1B—C14B—C19B—C18B | −178.4 (4) |
C17A—C18A—C19A—C14A | −0.7 (7) | C15B—C14B—C19B—Cl1B | −176.5 (3) |
C17A—C18A—C19A—Cl1A | −178.7 (4) | N1B—C14B—C19B—Cl1B | 2.4 (6) |
N13A—C12A—C21A—C26A | −45.9 (6) | N13B—C12B—C21B—C26B | 56.8 (6) |
N11A—C12A—C21A—C26A | 137.3 (4) | N11B—C12B—C21B—C26B | −125.1 (5) |
N13A—C12A—C21A—C22A | 130.9 (4) | N13B—C12B—C21B—C22B | −123.3 (5) |
N11A—C12A—C21A—C22A | −45.9 (6) | N11B—C12B—C21B—C22B | 54.8 (6) |
C26A—C21A—C22A—C23A | −2.0 (6) | C26B—C21B—C22B—C23B | 1.2 (7) |
C12A—C21A—C22A—C23A | −178.9 (4) | C12B—C21B—C22B—C23B | −178.7 (4) |
C21A—C22A—C23A—N24A | 2.1 (7) | C21B—C22B—C23B—N24B | 0.6 (8) |
C22A—C23A—N24A—C25A | −0.8 (7) | C22B—C23B—N24B—C25B | −1.7 (8) |
C23A—N24A—C25A—C26A | −0.6 (7) | C23B—N24B—C25B—C26B | 1.1 (8) |
C22A—C21A—C26A—C25A | 0.7 (7) | C22B—C21B—C26B—C25B | −1.7 (7) |
C12A—C21A—C26A—C25A | 177.6 (4) | C12B—C21B—C26B—C25B | 178.2 (4) |
N24A—C25A—C26A—C21A | 0.6 (7) | N24B—C25B—C26B—C21B | 0.6 (8) |
Compound | N13—N1—C14—C15 | N13—C12—C21—C26 |
(1) | -42.3 (4) | 53.6 (5) |
(2A) | -53.3 (5) | -45.9 (6) |
(2B) | -53.7 (5) | -56.8 (6) |
Acknowledgements
BAT thanks the Palestinian Research Council (Ramallah) for funding and HFU (Germany) for hosting.
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