research communications
Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione
aInstitut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, 09599 Freiberg/Sachsen, Germany
*Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de
The title compounds, C23H25Br2NO2 (1) and C31H29BrN2O4 (2), crystallize in the P21/n with two (1-A and 1-B) and one molecules, respectively, in the of the cell. The molecular conformation of these compounds is stabilized by intramolecular C—H⋯O hydrogen bonds and C—H⋯N or C—H⋯π interactions. The of 1 features a relatively strong Br⋯O=C halogen bond, which is not observed in the case of 2. Both crystal structures are characterized by the presence of C—H⋯Br hydrogen bonds and numerous intermolecular C—H⋯O hydrogen-bonding interactions.
1. Chemical context
Compounds consisting of a 1,3,5-trisubstituted 2,4,6-trialkylbenzene scaffold have been recognized to possess the ability to act as artificial receptors for various neutral and ionic substrates, such as , 2012), ion pairs (for example, hydronium/hydroxide ions; Stapf et al., 2015) and ammonium ions (Chin et al., 2002; Jonah et al., 2017; Schulze et al., 2018). In the case of carbohydrate-binding agents (artificial carbohydrate receptors), both acyclic (Kaiser et al. 2019; Stapf et al., 2020a, 2020b; Köhler et al., 2020) and macrocyclic compounds (Lippe & Mazik, 2013, 2015; Amrhein et al., 2016; Amrhein & Mazik, 2021) have been developed. Bromomethyl- and/or phthalimidomethyl-functionalized trialkylbenzenes are often used as precursors for the syntheses of such compounds . The crystal structures of two representatives of this class of compounds bearing both bromomethyl- and phthalimidomethyl groups are described in this work.
(Mazik, 20092. Structural commentary
Compounds 1 and 2, the structures of which are illustrated in Fig. 1, were found to crystallize in the monoclinic P21/n. In the case of compound 1, the of the cell consists of two crystallographically non-equivalent molecules (1-A and 1-B). Molecule 1-A displays a conformation with a fully alternating arrangement of the substituents above and below the plane of the central benzene ring [ab′ab′ab′ pattern, a = above, b = below (a′/b′ = Et above/below); see Koch et al., 2017; Schulze et al., 2017]. In molecule 1-B, one of the ethyl groups is disordered over two positions with an occupancy of 0.820 (6) for the major disorder component; the two disorder positions are related by rotation of approximately 180° about the C4—C11 bond. The molecules display similar conformations, as illustrated by the molecular least-squares overlay shown in Fig. 2. The dihedral angle between the phthalimide moiety and the benzene ring is 82.27 (14)° (molecule 1-A) and 83.78 (13)° (molecule 1-B). The conformation of the molecules appear to be stabilized by intramolecular C—H⋯O=C hydrogen bonds (Tables 1 and 2), which involve ethyl H atoms [d(H⋯O) = 2.59, 2.64 Å]. Furthermore, one ethyl group of each molecule participates in the formation of an intramolecular C—H⋯N bond with H⋯N distances of 2.45 and 2.54 Å, respectively.
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The 2 contains one molecule in the of the cell. The two phthalimide groups of the molecule point in opposite directions, showing inclination angles of 70.27 (16) and 79.10 (16)° with respect to the plane of the central aromatic ring. The three-dimensional arrangement of substituents along the periphery of the benzene ring follows an ab′ba′ab′ pattern, in which the bromomethyl group, one phthalimidomethyl unit and one ethyl group are directed towards one face of the benzene ring, whereas the three remaining substituents point in the opposite direction. This conformation is stabilized by intramolecular Cethyl—H⋯O=C (2.45, 2.50 Å) and Cethyl—H⋯π interactions [d(H⋯Cg) 2.80, 2.85 Å].
of compound3. Supramolecular features
In the crystal of compound 1, the distance of 3.220 (3) Å between Br2B and the oxygen atom O1A of an adjacent molecules (symmetry code: 1 + x, y, z) is considerably shorter than the sum of the van der Waals radii of the atoms (3.37 Å; Bondi, 1964); this, as well as the well-defined bond geometry [∠C—Br⋯O = 171.34 (11)°] indicates the presence of a relatively strong Br⋯O halogen bond (Table 3). This C—Br⋯O=C interaction is assisted by a C—H⋯Br bond [d(H⋯Br) = 2.92 Å, ∠C—H⋯Br = 141.6°], so that atom Br2B acts as a bifurcated binding site (see Fig. 3). The atoms Br1B and Br2A are involved in the formation of Cethyl—H⋯Br interactions with distances of 2.86 and 3.00 Å, respectively (∠C—H⋯Br = 123 and 158°). The two independent molecules are involved in a different way in the molecular association. The phthalimide group of molecule 1-B participates in the formation of C—H⋯π contacts with H⋯Cg distances of 2.62 and 2.96 Å, whereas the phthalimide moiety of the second molecule is involved in the formation of an offset face-to-face interaction [d(Cg⋯Cg) = 3.75 Å, symmetry code: −x, 1 − y, 1 − z]. In addition, the crystal packing is characterized by the presence of several C—H⋯O hydrogen bonds (2.35–2.43 Å; Table 1). The different types of non-covalent bonds in the crystal generate a three-dimensional supramolecular network.
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As a result of the presence of two phthalimide units in compound 2, its is dominated by C—H⋯O bonds [d(H⋯O) = 2.49–2.59 Å; Table 2] in which all oxygen atoms participate. The fragment of the packing structure shown in Fig. 4 shows that atoms O1 and H10A take part in the formation of an inversion-symmetric supramolecular ring motif with graph-set motif R22(10) (Etter, 1990; Bernstein et al., 1995; such a ten-membered supramolecular motif has, for example, been recognized in some crystal structures of fluorene derivatives bearing phthalimidomethyl groups, see Seidel et al., 2021). In addition, the molecules are linked by two C—H⋯π interactions [d(H⋯Cg = 2.84, 2.88 Å] with the C1–C6 and C12–C17 rings acting as acceptors.
4. Database survey
A search in the Cambridge Structural Database (CSD, Version 5.41, update of November 2019; Groom et al., 2016) for 2-benzylisoindoline-1,3-dione resulted in 48 hits. Regarding the description of crystal structures of tri- to hexasubstituted benzene derivatives, the number of hits could be reduced to three relevant entries. This includes two hexasubstituted benzene derivatives consisting of three isoindoline-1,3-dione groups (phthalimidomethyl groups) and either methoxy (IDOBIO; Rosien et al., 2013) or bromomethyl groups (LOFBIT; Koch et al., 2014) in each of the 2-, 4- and 6-positions of the benzene ring. Furthermore, a 1,3,5-trisubstituted benzene derivative, namely 3,5-bis(phthalimidomethyl)phenyl-tert-butyldimethylsilyl ether (WIKRAK; Domínguez et al., 2007), has been found. In the case of IDOBIO and LOFBIT, the molecules adopt a conformation in which two phthalimidomethyl groups and one methoxy or bromomethyl group are directed towards one face of the benzene ring. The phthalimidomethyl groups of the 1,3,5-trisubstituted benzene derivative adopt a trans geometry.
5. Synthesis and crystallization
A suspension of 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene (1.00 g, 2.27 mmol) and potassium phthalimide (0.84 g, 4.54 mmol) in a solvent mixture N,N-dimethylformamide/1,4-dioxane (15 ml, 2:1, v/v) was stirred at ambient temperature for 24 h. Afterwards, the reaction mixture was poured into 50 ml of water. The white precipitate was filtered off, washed several times with water and finally suspended in water. After extraction with chloroform (five times) and evaporation of the organic solvent, the crude product was purified by (SiO2; toluene/ethyl acetate). Compounds 1 and 2 were obtained as white solids.
Compound 1: Yield: 27%; m.p. 482 K (decomposition; toluene/ethyl acetate); Rf = 0.68 (SiO2; toluene/ethyl acetate 10:1 v/v); 1H NMR (500 MHz, CDCl3): 1.16 (t, 6H, J = 7.6 Hz), 1.35 (t, 3H, J = 7.6 Hz), 2.94 (q, 2H, J = 7.6 Hz), 3.03 (q, 4H, J = 7.6 Hz), 4.61 (s, 4H), 4.92 (s, 2H), 7.69–7.71 (m, 2H), 7.72–7.83 (m, 2H) ppm; 13C NMR (500 MHz, CDCl3): 15.6, 15.7, 22.8, 23.0, 29.1, 37.0, 123.3, 130.6, 131.9, 132.1, 134.1, 144.2, 145.8, 168.1 ppm; IR (ATR): 2969, 1709, 1491, 1454, 1392, 592 cm−1; LC–MS (ESI): calculated for C23H25Br2NO2Na (M + Na)+: 530.01, found: 530.21.
Compound 2: Yield: 40%; m.p. 494–495 K (toluene/ethyl acetate); Rf = 0.48 (SiO2; toluene/ethyl acetate 10:1 v/v); 1H NMR (500 MHz, CDCl3): 0.97 (t, 3H, J = 7.6 Hz), 1.14 (t, 6H, J = 7.6 Hz), 3.00 (q, 4H, J = 7.6 Hz), 3.18 (q, 2H, J = 7.6 Hz), 4.63 (s, 2H), 4.94 (s, 4H), 7.68–7.70 (m, 4H), 7.71–7.83 (m, 4H) ppm; 13C NMR (500 MHz, CDCl3): 15.7, 15.8, 23.0, 23.5, 29.7, 37.3, 123.3, 130.0, 131.7, 131.9, 134.0, 144.8, 146.5, 168.2 ppm; IR (ATR): 2962, 1700, 1498, 1463, 1392, 528 cm−1; LC–MS (ESI): calculated for C31H30BrN2O4 (M + H)+: 575.14, found: 575.06.
Single crystals suitable for X-ray diffraction were obtained by crystallization of the respective compound from toluene/ethyl acetate (1) and toluene (2).
6. Refinement
Crystal data, data collection and structure . All H atoms were positioned geometrically and refined as riding, with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.5 Ueq(C) for methyl groups or Uiso(H) = 1.2 Ueq(C) otherwise. For compound 1, one ethyl group (C11B–C12B/C11C–C12C) in 1-B was refined in two positions using EADP and EXYZ restraints.
details are summarized in Table 4
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Supporting information
https://doi.org/10.1107/S205698902100788X/zq2264sup1.cif
contains datablocks 1, 2, global. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S205698902100788X/zq22641sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S205698902100788X/zq22642sup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698902100788X/zq22641sup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S205698902100788X/zq22642sup5.cml
For both structures, data collection: X-AREA (Stoe, 2009); cell
X-AREA (Stoe, 2009); data reduction: X-RED (Stoe, 2009); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and shelXle (Hübschle et al., 2011).C23H25Br2NO2 | F(000) = 2048 |
Mr = 507.26 | Dx = 1.553 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.367 (2) Å | Cell parameters from 2236 reflections |
b = 19.966 (3) Å | θ = 2.6–25.7° |
c = 16.919 (4) Å | µ = 3.76 mm−1 |
β = 106.099 (15)° | T = 153 K |
V = 4338.5 (14) Å3 | Piece, colorless |
Z = 8 | 0.40 × 0.23 × 0.17 mm |
STOE IPDS 2T diffractometer | 8523 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 5961 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.067 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
rotation method scans | h = −16→16 |
Absorption correction: integration | k = −24→24 |
Tmin = 0.324, Tmax = 0.472 | l = −20→20 |
48044 measured reflections |
Refinement on F2 | 5 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0287P)2 + 3.7348P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
8523 reflections | Δρmax = 0.78 e Å−3 |
516 parameters | Δρmin = −0.85 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) | |
Br1A | 0.16416 (3) | 0.64628 (2) | 0.09609 (2) | 0.04094 (10) | |
Br2A | 0.55611 (3) | 0.52669 (2) | 0.36556 (3) | 0.05486 (13) | |
O1A | 0.1498 (2) | 0.36605 (13) | 0.49979 (14) | 0.0395 (6) | |
O2A | 0.1109 (2) | 0.57148 (12) | 0.37508 (16) | 0.0469 (7) | |
N1A | 0.1343 (2) | 0.46167 (13) | 0.41932 (16) | 0.0279 (6) | |
C1A | 0.2142 (2) | 0.51420 (15) | 0.16832 (19) | 0.0235 (7) | |
C2A | 0.3218 (2) | 0.50277 (15) | 0.19315 (19) | 0.0246 (7) | |
C3A | 0.3659 (2) | 0.46791 (15) | 0.26682 (19) | 0.0241 (7) | |
C4A | 0.3024 (2) | 0.44455 (15) | 0.31516 (18) | 0.0229 (7) | |
C5A | 0.1951 (2) | 0.45732 (15) | 0.29062 (18) | 0.0225 (7) | |
C6A | 0.1501 (2) | 0.49312 (15) | 0.21738 (18) | 0.0230 (7) | |
C7A | 0.1661 (3) | 0.54733 (15) | 0.0867 (2) | 0.0287 (7) | |
H7A | 0.093934 | 0.530854 | 0.064312 | 0.034* | |
H7B | 0.205959 | 0.534699 | 0.047632 | 0.034* | |
C8A | 0.3894 (3) | 0.52472 (18) | 0.1391 (2) | 0.0340 (8) | |
H8A | 0.459884 | 0.535976 | 0.174052 | 0.041* | |
H8B | 0.359230 | 0.565484 | 0.108240 | 0.041* | |
C9A | 0.3974 (3) | 0.4693 (2) | 0.0781 (2) | 0.0448 (10) | |
H9A | 0.441493 | 0.484750 | 0.044129 | 0.067* | |
H9B | 0.327785 | 0.458744 | 0.042768 | 0.067* | |
H9C | 0.428167 | 0.429159 | 0.108595 | 0.067* | |
C10A | 0.4810 (3) | 0.45441 (16) | 0.2934 (2) | 0.0308 (8) | |
H10A | 0.507217 | 0.450900 | 0.244241 | 0.037* | |
H10B | 0.494319 | 0.411194 | 0.323135 | 0.037* | |
C11A | 0.3497 (3) | 0.40134 (16) | 0.39013 (19) | 0.0269 (7) | |
H11A | 0.308225 | 0.406023 | 0.430053 | 0.032* | |
H11B | 0.421453 | 0.416754 | 0.417113 | 0.032* | |
C12A | 0.3520 (3) | 0.32768 (17) | 0.3655 (2) | 0.0347 (8) | |
H12A | 0.392091 | 0.301699 | 0.412842 | 0.052* | |
H12B | 0.384727 | 0.323864 | 0.320503 | 0.052* | |
H12C | 0.280706 | 0.310351 | 0.347287 | 0.052* | |
C13A | 0.1249 (3) | 0.42863 (16) | 0.33988 (19) | 0.0270 (7) | |
H13A | 0.051651 | 0.431931 | 0.306061 | 0.032* | |
H13B | 0.141356 | 0.380507 | 0.350038 | 0.032* | |
C14A | 0.1440 (3) | 0.42633 (18) | 0.4930 (2) | 0.0301 (8) | |
C15A | 0.1469 (3) | 0.47882 (19) | 0.5564 (2) | 0.0329 (8) | |
C16A | 0.1600 (3) | 0.4726 (2) | 0.6405 (2) | 0.0425 (9) | |
H16A | 0.165391 | 0.430161 | 0.666754 | 0.051* | |
C17A | 0.1650 (3) | 0.5332 (2) | 0.6847 (2) | 0.0499 (11) | |
H17A | 0.174875 | 0.531280 | 0.742489 | 0.060* | |
C18A | 0.1561 (3) | 0.5948 (2) | 0.6471 (3) | 0.0508 (10) | |
H18A | 0.160339 | 0.634344 | 0.679134 | 0.061* | |
C19A | 0.1409 (3) | 0.5999 (2) | 0.5630 (2) | 0.0464 (10) | |
H19A | 0.133774 | 0.642245 | 0.536402 | 0.056* | |
C20A | 0.1366 (3) | 0.54083 (18) | 0.5190 (2) | 0.0345 (8) | |
C21A | 0.1250 (3) | 0.53045 (18) | 0.4296 (2) | 0.0328 (8) | |
C22A | 0.0342 (2) | 0.50790 (17) | 0.1894 (2) | 0.0286 (7) | |
H22A | 0.022597 | 0.549713 | 0.156644 | 0.034* | |
H22B | 0.008679 | 0.515234 | 0.238308 | 0.034* | |
C23A | −0.0282 (3) | 0.45160 (19) | 0.1379 (2) | 0.0377 (9) | |
H23A | −0.101033 | 0.465459 | 0.116564 | 0.057* | |
H23B | −0.024207 | 0.411552 | 0.172112 | 0.057* | |
H23C | 0.000531 | 0.441538 | 0.091847 | 0.057* | |
Br1B | 0.67396 (3) | 0.39932 (2) | 0.09585 (2) | 0.04119 (10) | |
Br2B | 1.04422 (3) | 0.25251 (2) | 0.36780 (2) | 0.03582 (9) | |
O1B | 0.6272 (2) | 0.11607 (13) | 0.48916 (16) | 0.0435 (7) | |
O2B | 0.61521 (19) | 0.32716 (12) | 0.38071 (14) | 0.0350 (6) | |
N1B | 0.6197 (2) | 0.21507 (14) | 0.41532 (16) | 0.0300 (6) | |
C1B | 0.7055 (2) | 0.26581 (14) | 0.16601 (18) | 0.0225 (7) | |
C2B | 0.8113 (2) | 0.24748 (15) | 0.19156 (18) | 0.0234 (6) | |
C3B | 0.8472 (2) | 0.20833 (15) | 0.26292 (18) | 0.0236 (7) | |
C4B | 0.7787 (3) | 0.18849 (15) | 0.30865 (19) | 0.0252 (7) | |
C5B | 0.6737 (2) | 0.20943 (15) | 0.28466 (19) | 0.0245 (7) | |
C6B | 0.6371 (2) | 0.24923 (16) | 0.21354 (18) | 0.0249 (7) | |
C7B | 0.6642 (3) | 0.30068 (16) | 0.0850 (2) | 0.0295 (7) | |
H7C | 0.590476 | 0.287854 | 0.060999 | 0.035* | |
H7D | 0.703943 | 0.285679 | 0.046832 | 0.035* | |
C8B | 0.8845 (3) | 0.26902 (16) | 0.14208 (19) | 0.0279 (7) | |
H8C | 0.954519 | 0.277115 | 0.179979 | 0.033* | |
H8D | 0.859366 | 0.311679 | 0.113665 | 0.033* | |
C9B | 0.8929 (3) | 0.21651 (19) | 0.0782 (2) | 0.0359 (8) | |
H9D | 0.939746 | 0.232899 | 0.047079 | 0.054* | |
H9E | 0.823776 | 0.208315 | 0.040526 | 0.054* | |
H9F | 0.920501 | 0.174702 | 0.106241 | 0.054* | |
C10B | 0.9591 (3) | 0.18730 (17) | 0.2891 (2) | 0.0300 (7) | |
H10C | 0.985816 | 0.183927 | 0.240246 | 0.036* | |
H10D | 0.964949 | 0.142577 | 0.315289 | 0.036* | |
C11B | 0.8180 (3) | 0.14231 (16) | 0.3819 (2) | 0.0311 (8) | 0.820 (6) |
H11C | 0.891146 | 0.153595 | 0.410628 | 0.037* | 0.820 (6) |
H11D | 0.775821 | 0.148948 | 0.421073 | 0.037* | 0.820 (6) |
C12B | 0.8113 (4) | 0.0699 (2) | 0.3550 (3) | 0.0406 (12) | 0.820 (6) |
H12D | 0.848945 | 0.041825 | 0.401198 | 0.061* | 0.820 (6) |
H12E | 0.842563 | 0.064919 | 0.309354 | 0.061* | 0.820 (6) |
H12F | 0.738156 | 0.056104 | 0.337049 | 0.061* | 0.820 (6) |
C11C | 0.8180 (3) | 0.14231 (16) | 0.3819 (2) | 0.0311 (8) | 0.180 (6) |
H11E | 0.758897 | 0.115163 | 0.388690 | 0.037* | 0.180 (6) |
H11F | 0.869688 | 0.111156 | 0.370233 | 0.037* | 0.180 (6) |
C12C | 0.8641 (17) | 0.1758 (10) | 0.4567 (12) | 0.0406 (12) | 0.180 (6) |
H12G | 0.932253 | 0.193439 | 0.455771 | 0.061* | 0.180 (6) |
H12H | 0.872996 | 0.144431 | 0.502612 | 0.061* | 0.180 (6) |
H12I | 0.819208 | 0.212918 | 0.463481 | 0.061* | 0.180 (6) |
C13B | 0.5994 (3) | 0.18597 (17) | 0.3324 (2) | 0.0330 (8) | |
H13C | 0.527408 | 0.197432 | 0.300662 | 0.040* | |
H13D | 0.603806 | 0.136584 | 0.337432 | 0.040* | |
C14B | 0.6311 (3) | 0.17670 (19) | 0.4873 (2) | 0.0333 (8) | |
C15B | 0.6500 (3) | 0.22625 (19) | 0.5562 (2) | 0.0335 (8) | |
C16B | 0.6689 (3) | 0.2166 (2) | 0.6403 (2) | 0.0412 (9) | |
H16B | 0.671296 | 0.173089 | 0.663423 | 0.049* | |
C17B | 0.6840 (3) | 0.2739 (2) | 0.6891 (2) | 0.0480 (10) | |
H17B | 0.696999 | 0.269143 | 0.746899 | 0.058* | |
C18B | 0.6808 (3) | 0.3374 (2) | 0.6561 (2) | 0.0464 (10) | |
H18B | 0.691568 | 0.375124 | 0.691637 | 0.056* | |
C19B | 0.6621 (3) | 0.3470 (2) | 0.5715 (2) | 0.0398 (9) | |
H19B | 0.659735 | 0.390576 | 0.548338 | 0.048* | |
C20B | 0.6471 (2) | 0.29004 (18) | 0.5229 (2) | 0.0305 (8) | |
C21B | 0.6258 (3) | 0.28343 (18) | 0.4321 (2) | 0.0300 (7) | |
C22B | 0.5264 (2) | 0.27532 (17) | 0.1873 (2) | 0.0303 (7) | |
H22C | 0.525540 | 0.319108 | 0.159625 | 0.036* | |
H22D | 0.502198 | 0.282707 | 0.236834 | 0.036* | |
C23B | 0.4509 (3) | 0.2279 (2) | 0.1292 (3) | 0.0509 (10) | |
H23D | 0.382770 | 0.249568 | 0.109135 | 0.076* | |
H23E | 0.443652 | 0.186717 | 0.158665 | 0.076* | |
H23F | 0.477779 | 0.216890 | 0.082429 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1A | 0.0464 (2) | 0.02807 (18) | 0.0440 (2) | 0.00305 (16) | 0.00543 (18) | 0.01000 (16) |
Br2A | 0.0321 (2) | 0.0477 (2) | 0.0728 (3) | −0.00696 (19) | −0.0055 (2) | −0.0089 (2) |
O1A | 0.0469 (16) | 0.0415 (16) | 0.0306 (13) | 0.0038 (12) | 0.0115 (12) | 0.0086 (11) |
O2A | 0.071 (2) | 0.0318 (14) | 0.0397 (15) | −0.0018 (13) | 0.0188 (14) | −0.0002 (12) |
N1A | 0.0324 (16) | 0.0302 (15) | 0.0227 (15) | 0.0005 (12) | 0.0101 (12) | −0.0010 (11) |
C1A | 0.0253 (17) | 0.0222 (16) | 0.0208 (16) | 0.0018 (13) | 0.0025 (14) | −0.0012 (12) |
C2A | 0.0266 (17) | 0.0223 (16) | 0.0258 (17) | −0.0007 (13) | 0.0088 (14) | 0.0017 (13) |
C3A | 0.0245 (17) | 0.0196 (15) | 0.0269 (17) | 0.0006 (13) | 0.0050 (14) | −0.0006 (13) |
C4A | 0.0255 (17) | 0.0202 (15) | 0.0212 (16) | 0.0011 (13) | 0.0038 (14) | 0.0005 (12) |
C5A | 0.0266 (17) | 0.0221 (16) | 0.0197 (16) | −0.0018 (13) | 0.0077 (14) | −0.0040 (12) |
C6A | 0.0236 (17) | 0.0225 (16) | 0.0228 (16) | −0.0021 (13) | 0.0064 (13) | −0.0041 (12) |
C7A | 0.0315 (19) | 0.0252 (17) | 0.0277 (18) | −0.0023 (14) | 0.0053 (15) | 0.0015 (13) |
C8A | 0.0294 (19) | 0.040 (2) | 0.036 (2) | 0.0003 (16) | 0.0132 (16) | 0.0146 (16) |
C9A | 0.045 (2) | 0.060 (3) | 0.037 (2) | 0.012 (2) | 0.0224 (19) | 0.0108 (19) |
C10A | 0.0281 (18) | 0.0292 (18) | 0.0348 (19) | 0.0012 (14) | 0.0085 (16) | 0.0042 (14) |
C11A | 0.0277 (18) | 0.0311 (18) | 0.0218 (16) | 0.0030 (14) | 0.0064 (14) | 0.0042 (13) |
C12A | 0.042 (2) | 0.0290 (18) | 0.035 (2) | 0.0035 (16) | 0.0134 (17) | 0.0081 (15) |
C13A | 0.0275 (18) | 0.0289 (17) | 0.0242 (17) | −0.0044 (14) | 0.0067 (14) | −0.0029 (13) |
C14A | 0.0238 (18) | 0.039 (2) | 0.0276 (18) | 0.0007 (15) | 0.0073 (15) | 0.0033 (15) |
C15A | 0.0201 (17) | 0.052 (2) | 0.0268 (18) | 0.0008 (16) | 0.0077 (15) | −0.0071 (16) |
C16A | 0.030 (2) | 0.069 (3) | 0.030 (2) | 0.0015 (19) | 0.0101 (17) | 0.0015 (18) |
C17A | 0.034 (2) | 0.088 (3) | 0.028 (2) | 0.000 (2) | 0.0076 (18) | −0.021 (2) |
C18A | 0.043 (2) | 0.063 (3) | 0.046 (2) | 0.001 (2) | 0.011 (2) | −0.018 (2) |
C19A | 0.048 (2) | 0.051 (2) | 0.041 (2) | −0.002 (2) | 0.0139 (19) | −0.0153 (18) |
C20A | 0.0280 (19) | 0.043 (2) | 0.033 (2) | −0.0020 (16) | 0.0103 (16) | −0.0088 (16) |
C21A | 0.032 (2) | 0.0351 (19) | 0.032 (2) | −0.0004 (16) | 0.0108 (16) | −0.0045 (16) |
C22A | 0.0253 (18) | 0.0331 (18) | 0.0270 (17) | 0.0023 (14) | 0.0065 (15) | 0.0018 (14) |
C23A | 0.030 (2) | 0.047 (2) | 0.0321 (19) | −0.0074 (16) | 0.0024 (16) | −0.0016 (16) |
Br1B | 0.0400 (2) | 0.03334 (19) | 0.0493 (2) | 0.00394 (16) | 0.01081 (18) | 0.01429 (17) |
Br2B | 0.02973 (18) | 0.03980 (19) | 0.03393 (18) | −0.00315 (16) | 0.00217 (14) | 0.00055 (16) |
O1B | 0.0527 (17) | 0.0392 (16) | 0.0448 (16) | 0.0032 (12) | 0.0235 (14) | 0.0156 (12) |
O2B | 0.0387 (15) | 0.0312 (13) | 0.0352 (14) | 0.0064 (11) | 0.0103 (12) | 0.0097 (11) |
N1B | 0.0348 (16) | 0.0324 (16) | 0.0262 (15) | 0.0013 (13) | 0.0143 (13) | 0.0062 (12) |
C1B | 0.0263 (17) | 0.0190 (16) | 0.0208 (15) | −0.0025 (12) | 0.0040 (13) | −0.0025 (12) |
C2B | 0.0260 (16) | 0.0220 (15) | 0.0222 (15) | −0.0020 (13) | 0.0069 (13) | −0.0037 (13) |
C3B | 0.0257 (17) | 0.0216 (16) | 0.0225 (16) | 0.0028 (13) | 0.0050 (14) | −0.0008 (12) |
C4B | 0.0316 (18) | 0.0207 (16) | 0.0233 (17) | 0.0031 (13) | 0.0078 (14) | 0.0008 (13) |
C5B | 0.0286 (18) | 0.0226 (16) | 0.0237 (16) | −0.0018 (13) | 0.0098 (14) | −0.0008 (13) |
C6B | 0.0250 (16) | 0.0229 (15) | 0.0249 (16) | −0.0033 (14) | 0.0038 (13) | −0.0046 (13) |
C7B | 0.0294 (18) | 0.0323 (18) | 0.0255 (18) | −0.0010 (15) | 0.0051 (15) | 0.0039 (14) |
C8B | 0.0226 (17) | 0.0338 (19) | 0.0263 (17) | −0.0036 (14) | 0.0055 (14) | 0.0015 (13) |
C9B | 0.035 (2) | 0.047 (2) | 0.0301 (19) | −0.0016 (17) | 0.0163 (17) | −0.0055 (16) |
C10B | 0.0308 (19) | 0.0307 (18) | 0.0270 (18) | 0.0026 (14) | 0.0053 (15) | 0.0007 (14) |
C11B | 0.034 (2) | 0.0302 (18) | 0.0283 (18) | 0.0065 (15) | 0.0074 (15) | 0.0040 (14) |
C12B | 0.060 (3) | 0.026 (2) | 0.036 (2) | 0.003 (2) | 0.014 (2) | 0.0077 (18) |
C11C | 0.034 (2) | 0.0302 (18) | 0.0283 (18) | 0.0065 (15) | 0.0074 (15) | 0.0040 (14) |
C12C | 0.060 (3) | 0.026 (2) | 0.036 (2) | 0.003 (2) | 0.014 (2) | 0.0077 (18) |
C13B | 0.036 (2) | 0.0332 (19) | 0.0325 (19) | 0.0000 (15) | 0.0147 (16) | 0.0054 (15) |
C14B | 0.031 (2) | 0.040 (2) | 0.034 (2) | 0.0050 (16) | 0.0170 (17) | 0.0130 (16) |
C15B | 0.0236 (18) | 0.050 (2) | 0.0293 (19) | 0.0047 (16) | 0.0111 (15) | 0.0062 (16) |
C16B | 0.034 (2) | 0.059 (3) | 0.033 (2) | 0.0056 (18) | 0.0145 (17) | 0.0122 (19) |
C17B | 0.041 (2) | 0.077 (3) | 0.026 (2) | 0.011 (2) | 0.0108 (18) | 0.004 (2) |
C18B | 0.039 (2) | 0.066 (3) | 0.034 (2) | 0.005 (2) | 0.0099 (18) | −0.0076 (19) |
C19B | 0.031 (2) | 0.045 (2) | 0.045 (2) | 0.0006 (17) | 0.0140 (18) | −0.0004 (17) |
C20B | 0.0223 (17) | 0.040 (2) | 0.0304 (19) | 0.0032 (15) | 0.0097 (15) | 0.0057 (15) |
C21B | 0.0229 (17) | 0.0359 (19) | 0.0326 (19) | 0.0040 (15) | 0.0100 (15) | 0.0045 (16) |
C22B | 0.0241 (17) | 0.0311 (18) | 0.0345 (19) | 0.0001 (14) | 0.0063 (15) | 0.0018 (14) |
C23B | 0.029 (2) | 0.063 (3) | 0.057 (3) | −0.0114 (19) | 0.0056 (19) | −0.004 (2) |
Br1A—C7A | 1.983 (3) | N1B—C21B | 1.392 (4) |
Br2A—C10A | 1.975 (3) | N1B—C14B | 1.411 (4) |
O1A—C14A | 1.210 (4) | N1B—C13B | 1.472 (4) |
O2A—C21A | 1.208 (4) | C1B—C2B | 1.407 (4) |
N1A—C21A | 1.394 (4) | C1B—C6B | 1.415 (4) |
N1A—C14A | 1.406 (4) | C1B—C7B | 1.499 (4) |
N1A—C13A | 1.471 (4) | C2B—C3B | 1.406 (4) |
C1A—C2A | 1.401 (4) | C2B—C8B | 1.516 (4) |
C1A—C6A | 1.412 (4) | C3B—C4B | 1.409 (4) |
C1A—C7A | 1.505 (4) | C3B—C10B | 1.498 (4) |
C2A—C3A | 1.406 (4) | C4B—C5B | 1.412 (4) |
C2A—C8A | 1.517 (4) | C4B—C11C | 1.517 (4) |
C3A—C4A | 1.411 (4) | C4B—C11B | 1.517 (4) |
C3A—C10A | 1.503 (4) | C5B—C6B | 1.411 (4) |
C4A—C5A | 1.402 (4) | C5B—C13B | 1.518 (4) |
C4A—C11A | 1.519 (4) | C6B—C22B | 1.514 (4) |
C5A—C6A | 1.412 (4) | C7B—H7C | 0.9900 |
C5A—C13A | 1.528 (4) | C7B—H7D | 0.9900 |
C6A—C22A | 1.518 (4) | C8B—C9B | 1.532 (4) |
C7A—H7A | 0.9900 | C8B—H8C | 0.9900 |
C7A—H7B | 0.9900 | C8B—H8D | 0.9900 |
C8A—C9A | 1.536 (5) | C9B—H9D | 0.9800 |
C8A—H8A | 0.9900 | C9B—H9E | 0.9800 |
C8A—H8B | 0.9900 | C9B—H9F | 0.9800 |
C9A—H9A | 0.9800 | C10B—H10C | 0.9900 |
C9A—H9B | 0.9800 | C10B—H10D | 0.9900 |
C9A—H9C | 0.9800 | C11B—C12B | 1.510 (5) |
C10A—H10A | 0.9900 | C11B—H11C | 0.9900 |
C10A—H10B | 0.9900 | C11B—H11D | 0.9900 |
C11A—C12A | 1.531 (5) | C12B—H12D | 0.9800 |
C11A—H11A | 0.9900 | C12B—H12E | 0.9800 |
C11A—H11B | 0.9900 | C12B—H12F | 0.9800 |
C12A—H12A | 0.9800 | C11C—C12C | 1.41 (2) |
C12A—H12B | 0.9800 | C11C—H11E | 0.9900 |
C12A—H12C | 0.9800 | C11C—H11F | 0.9900 |
C13A—H13A | 0.9900 | C12C—H12G | 0.9800 |
C13A—H13B | 0.9900 | C12C—H12H | 0.9800 |
C14A—C15A | 1.493 (5) | C12C—H12I | 0.9800 |
C15A—C20A | 1.380 (5) | C13B—H13C | 0.9900 |
C15A—C16A | 1.390 (5) | C13B—H13D | 0.9900 |
C16A—C17A | 1.414 (6) | C14B—C15B | 1.496 (5) |
C16A—H16A | 0.9500 | C15B—C16B | 1.388 (5) |
C17A—C18A | 1.375 (6) | C15B—C20B | 1.389 (5) |
C17A—H17A | 0.9500 | C16B—C17B | 1.392 (6) |
C18A—C19A | 1.384 (6) | C16B—H16B | 0.9500 |
C18A—H18A | 0.9500 | C17B—C18B | 1.380 (6) |
C19A—C20A | 1.387 (5) | C17B—H17B | 0.9500 |
C19A—H19A | 0.9500 | C18B—C19B | 1.398 (5) |
C20A—C21A | 1.491 (5) | C18B—H18B | 0.9500 |
C22A—C23A | 1.521 (5) | C19B—C20B | 1.385 (5) |
C22A—H22A | 0.9900 | C19B—H19B | 0.9500 |
C22A—H22B | 0.9900 | C20B—C21B | 1.488 (5) |
C23A—H23A | 0.9800 | C22B—C23B | 1.527 (5) |
C23A—H23B | 0.9800 | C22B—H22C | 0.9900 |
C23A—H23C | 0.9800 | C22B—H22D | 0.9900 |
Br1B—C7B | 1.979 (3) | C23B—H23D | 0.9800 |
Br2B—C10B | 1.980 (3) | C23B—H23E | 0.9800 |
O1B—C14B | 1.212 (4) | C23B—H23F | 0.9800 |
O2B—C21B | 1.213 (4) | ||
C21A—N1A—C14A | 111.9 (3) | C3B—C2B—C8B | 120.9 (3) |
C21A—N1A—C13A | 124.6 (3) | C1B—C2B—C8B | 120.3 (3) |
C14A—N1A—C13A | 123.2 (3) | C2B—C3B—C4B | 120.6 (3) |
C2A—C1A—C6A | 121.0 (3) | C2B—C3B—C10B | 119.0 (3) |
C2A—C1A—C7A | 119.3 (3) | C4B—C3B—C10B | 120.4 (3) |
C6A—C1A—C7A | 119.7 (3) | C3B—C4B—C5B | 120.3 (3) |
C1A—C2A—C3A | 119.3 (3) | C3B—C4B—C11C | 119.3 (3) |
C1A—C2A—C8A | 120.3 (3) | C5B—C4B—C11C | 120.4 (3) |
C3A—C2A—C8A | 120.3 (3) | C3B—C4B—C11B | 119.3 (3) |
C2A—C3A—C4A | 120.4 (3) | C5B—C4B—C11B | 120.4 (3) |
C2A—C3A—C10A | 119.7 (3) | C6B—C5B—C4B | 119.6 (3) |
C4A—C3A—C10A | 119.9 (3) | C6B—C5B—C13B | 120.3 (3) |
C5A—C4A—C3A | 119.9 (3) | C4B—C5B—C13B | 120.0 (3) |
C5A—C4A—C11A | 120.3 (3) | C5B—C6B—C1B | 119.4 (3) |
C3A—C4A—C11A | 119.6 (3) | C5B—C6B—C22B | 121.6 (3) |
C4A—C5A—C6A | 120.2 (3) | C1B—C6B—C22B | 119.1 (3) |
C4A—C5A—C13A | 120.2 (3) | C1B—C7B—Br1B | 112.3 (2) |
C6A—C5A—C13A | 119.5 (3) | C1B—C7B—H7C | 109.1 |
C1A—C6A—C5A | 119.1 (3) | Br1B—C7B—H7C | 109.1 |
C1A—C6A—C22A | 119.5 (3) | C1B—C7B—H7D | 109.1 |
C5A—C6A—C22A | 121.4 (3) | Br1B—C7B—H7D | 109.1 |
C1A—C7A—Br1A | 112.1 (2) | H7C—C7B—H7D | 107.9 |
C1A—C7A—H7A | 109.2 | C2B—C8B—C9B | 112.3 (3) |
Br1A—C7A—H7A | 109.2 | C2B—C8B—H8C | 109.1 |
C1A—C7A—H7B | 109.2 | C9B—C8B—H8C | 109.1 |
Br1A—C7A—H7B | 109.2 | C2B—C8B—H8D | 109.1 |
H7A—C7A—H7B | 107.9 | C9B—C8B—H8D | 109.1 |
C2A—C8A—C9A | 111.2 (3) | H8C—C8B—H8D | 107.9 |
C2A—C8A—H8A | 109.4 | C8B—C9B—H9D | 109.5 |
C9A—C8A—H8A | 109.4 | C8B—C9B—H9E | 109.5 |
C2A—C8A—H8B | 109.4 | H9D—C9B—H9E | 109.5 |
C9A—C8A—H8B | 109.4 | C8B—C9B—H9F | 109.5 |
H8A—C8A—H8B | 108.0 | H9D—C9B—H9F | 109.5 |
C8A—C9A—H9A | 109.5 | H9E—C9B—H9F | 109.5 |
C8A—C9A—H9B | 109.5 | C3B—C10B—Br2B | 110.8 (2) |
H9A—C9A—H9B | 109.5 | C3B—C10B—H10C | 109.5 |
C8A—C9A—H9C | 109.5 | Br2B—C10B—H10C | 109.5 |
H9A—C9A—H9C | 109.5 | C3B—C10B—H10D | 109.5 |
H9B—C9A—H9C | 109.5 | Br2B—C10B—H10D | 109.5 |
C3A—C10A—Br2A | 110.9 (2) | H10C—C10B—H10D | 108.1 |
C3A—C10A—H10A | 109.5 | C12B—C11B—C4B | 110.9 (3) |
Br2A—C10A—H10A | 109.5 | C12B—C11B—H11C | 109.5 |
C3A—C10A—H10B | 109.5 | C4B—C11B—H11C | 109.5 |
Br2A—C10A—H10B | 109.5 | C12B—C11B—H11D | 109.5 |
H10A—C10A—H10B | 108.1 | C4B—C11B—H11D | 109.5 |
C4A—C11A—C12A | 110.7 (3) | H11C—C11B—H11D | 108.0 |
C4A—C11A—H11A | 109.5 | C11B—C12B—H12D | 109.5 |
C12A—C11A—H11A | 109.5 | C11B—C12B—H12E | 109.5 |
C4A—C11A—H11B | 109.5 | H12D—C12B—H12E | 109.5 |
C12A—C11A—H11B | 109.5 | C11B—C12B—H12F | 109.5 |
H11A—C11A—H11B | 108.1 | H12D—C12B—H12F | 109.5 |
C11A—C12A—H12A | 109.5 | H12E—C12B—H12F | 109.5 |
C11A—C12A—H12B | 109.5 | C12C—C11C—C4B | 114.2 (8) |
H12A—C12A—H12B | 109.5 | C12C—C11C—H11E | 108.7 |
C11A—C12A—H12C | 109.5 | C4B—C11C—H11E | 108.7 |
H12A—C12A—H12C | 109.5 | C12C—C11C—H11F | 108.7 |
H12B—C12A—H12C | 109.5 | C4B—C11C—H11F | 108.7 |
N1A—C13A—C5A | 114.9 (3) | H11E—C11C—H11F | 107.6 |
N1A—C13A—H13A | 108.5 | C11C—C12C—H12G | 109.5 |
C5A—C13A—H13A | 108.5 | C11C—C12C—H12H | 109.5 |
N1A—C13A—H13B | 108.5 | H12G—C12C—H12H | 109.5 |
C5A—C13A—H13B | 108.5 | C11C—C12C—H12I | 109.5 |
H13A—C13A—H13B | 107.5 | H12G—C12C—H12I | 109.5 |
O1A—C14A—N1A | 124.9 (3) | H12H—C12C—H12I | 109.5 |
O1A—C14A—C15A | 129.9 (3) | N1B—C13B—C5B | 114.2 (3) |
N1A—C14A—C15A | 105.2 (3) | N1B—C13B—H13C | 108.7 |
C20A—C15A—C16A | 121.2 (3) | C5B—C13B—H13C | 108.7 |
C20A—C15A—C14A | 108.7 (3) | N1B—C13B—H13D | 108.7 |
C16A—C15A—C14A | 130.1 (4) | C5B—C13B—H13D | 108.7 |
C15A—C16A—C17A | 116.0 (4) | H13C—C13B—H13D | 107.6 |
C15A—C16A—H16A | 122.0 | O1B—C14B—N1B | 124.7 (3) |
C17A—C16A—H16A | 122.0 | O1B—C14B—C15B | 129.8 (3) |
C18A—C17A—C16A | 122.4 (4) | N1B—C14B—C15B | 105.5 (3) |
C18A—C17A—H17A | 118.8 | C16B—C15B—C20B | 121.3 (4) |
C16A—C17A—H17A | 118.8 | C16B—C15B—C14B | 130.6 (3) |
C17A—C18A—C19A | 120.7 (4) | C20B—C15B—C14B | 108.1 (3) |
C17A—C18A—H18A | 119.7 | C15B—C16B—C17B | 116.7 (4) |
C19A—C18A—H18A | 119.7 | C15B—C16B—H16B | 121.7 |
C18A—C19A—C20A | 117.5 (4) | C17B—C16B—H16B | 121.7 |
C18A—C19A—H19A | 121.2 | C18B—C17B—C16B | 122.1 (4) |
C20A—C19A—H19A | 121.2 | C18B—C17B—H17B | 118.9 |
C15A—C20A—C19A | 122.1 (3) | C16B—C17B—H17B | 118.9 |
C15A—C20A—C21A | 108.1 (3) | C17B—C18B—C19B | 121.2 (4) |
C19A—C20A—C21A | 129.8 (4) | C17B—C18B—H18B | 119.4 |
O2A—C21A—N1A | 125.0 (3) | C19B—C18B—H18B | 119.4 |
O2A—C21A—C20A | 129.1 (3) | C20B—C19B—C18B | 116.7 (4) |
N1A—C21A—C20A | 106.0 (3) | C20B—C19B—H19B | 121.6 |
C6A—C22A—C23A | 112.6 (3) | C18B—C19B—H19B | 121.6 |
C6A—C22A—H22A | 109.1 | C19B—C20B—C15B | 122.0 (3) |
C23A—C22A—H22A | 109.1 | C19B—C20B—C21B | 129.8 (3) |
C6A—C22A—H22B | 109.1 | C15B—C20B—C21B | 108.2 (3) |
C23A—C22A—H22B | 109.1 | O2B—C21B—N1B | 124.8 (3) |
H22A—C22A—H22B | 107.8 | O2B—C21B—C20B | 128.8 (3) |
C22A—C23A—H23A | 109.5 | N1B—C21B—C20B | 106.3 (3) |
C22A—C23A—H23B | 109.5 | C6B—C22B—C23B | 113.1 (3) |
H23A—C23A—H23B | 109.5 | C6B—C22B—H22C | 108.9 |
C22A—C23A—H23C | 109.5 | C23B—C22B—H22C | 108.9 |
H23A—C23A—H23C | 109.5 | C6B—C22B—H22D | 108.9 |
H23B—C23A—H23C | 109.5 | C23B—C22B—H22D | 108.9 |
C21B—N1B—C14B | 111.7 (3) | H22C—C22B—H22D | 107.8 |
C21B—N1B—C13B | 124.5 (3) | C22B—C23B—H23D | 109.5 |
C14B—N1B—C13B | 123.8 (3) | C22B—C23B—H23E | 109.5 |
C2B—C1B—C6B | 121.2 (3) | H23D—C23B—H23E | 109.5 |
C2B—C1B—C7B | 119.1 (3) | C22B—C23B—H23F | 109.5 |
C6B—C1B—C7B | 119.7 (3) | H23D—C23B—H23F | 109.5 |
C3B—C2B—C1B | 118.9 (3) | H23E—C23B—H23F | 109.5 |
C6A—C1A—C2A—C3A | 2.0 (5) | C7B—C1B—C2B—C8B | 6.2 (4) |
C7A—C1A—C2A—C3A | −175.9 (3) | C1B—C2B—C3B—C4B | −0.8 (4) |
C6A—C1A—C2A—C8A | 179.0 (3) | C8B—C2B—C3B—C4B | 180.0 (3) |
C7A—C1A—C2A—C8A | 1.1 (4) | C1B—C2B—C3B—C10B | 178.5 (3) |
C1A—C2A—C3A—C4A | 0.1 (5) | C8B—C2B—C3B—C10B | −0.7 (4) |
C8A—C2A—C3A—C4A | −176.9 (3) | C2B—C3B—C4B—C5B | −1.9 (5) |
C1A—C2A—C3A—C10A | 179.0 (3) | C10B—C3B—C4B—C5B | 178.8 (3) |
C8A—C2A—C3A—C10A | 2.0 (5) | C2B—C3B—C4B—C11C | 175.8 (3) |
C2A—C3A—C4A—C5A | −1.3 (4) | C10B—C3B—C4B—C11C | −3.5 (4) |
C10A—C3A—C4A—C5A | 179.8 (3) | C2B—C3B—C4B—C11B | 175.8 (3) |
C2A—C3A—C4A—C11A | 174.2 (3) | C10B—C3B—C4B—C11B | −3.5 (4) |
C10A—C3A—C4A—C11A | −4.7 (4) | C3B—C4B—C5B—C6B | 1.3 (5) |
C3A—C4A—C5A—C6A | 0.4 (4) | C11C—C4B—C5B—C6B | −176.4 (3) |
C11A—C4A—C5A—C6A | −175.1 (3) | C11B—C4B—C5B—C6B | −176.4 (3) |
C3A—C4A—C5A—C13A | 176.4 (3) | C3B—C4B—C5B—C13B | 177.9 (3) |
C11A—C4A—C5A—C13A | 0.9 (4) | C11C—C4B—C5B—C13B | 0.2 (4) |
C2A—C1A—C6A—C5A | −2.9 (4) | C11B—C4B—C5B—C13B | 0.2 (4) |
C7A—C1A—C6A—C5A | 175.0 (3) | C4B—C5B—C6B—C1B | 1.9 (4) |
C2A—C1A—C6A—C22A | 178.5 (3) | C13B—C5B—C6B—C1B | −174.7 (3) |
C7A—C1A—C6A—C22A | −3.6 (4) | C4B—C5B—C6B—C22B | −177.4 (3) |
C4A—C5A—C6A—C1A | 1.7 (4) | C13B—C5B—C6B—C22B | 6.0 (4) |
C13A—C5A—C6A—C1A | −174.3 (3) | C2B—C1B—C6B—C5B | −4.7 (4) |
C4A—C5A—C6A—C22A | −179.8 (3) | C7B—C1B—C6B—C5B | 172.4 (3) |
C13A—C5A—C6A—C22A | 4.2 (4) | C2B—C1B—C6B—C22B | 174.7 (3) |
C2A—C1A—C7A—Br1A | −89.3 (3) | C7B—C1B—C6B—C22B | −8.2 (4) |
C6A—C1A—C7A—Br1A | 92.8 (3) | C2B—C1B—C7B—Br1B | −90.8 (3) |
C1A—C2A—C8A—C9A | −89.4 (4) | C6B—C1B—C7B—Br1B | 92.0 (3) |
C3A—C2A—C8A—C9A | 87.6 (4) | C3B—C2B—C8B—C9B | 86.8 (4) |
C2A—C3A—C10A—Br2A | 91.8 (3) | C1B—C2B—C8B—C9B | −92.4 (4) |
C4A—C3A—C10A—Br2A | −89.3 (3) | C2B—C3B—C10B—Br2B | 92.4 (3) |
C5A—C4A—C11A—C12A | 90.8 (3) | C4B—C3B—C10B—Br2B | −88.3 (3) |
C3A—C4A—C11A—C12A | −84.7 (4) | C3B—C4B—C11B—C12B | −84.5 (4) |
C21A—N1A—C13A—C5A | 52.9 (4) | C5B—C4B—C11B—C12B | 93.2 (4) |
C14A—N1A—C13A—C5A | −133.3 (3) | C3B—C4B—C11C—C12C | 87.7 (10) |
C4A—C5A—C13A—N1A | 73.6 (4) | C5B—C4B—C11C—C12C | −94.6 (10) |
C6A—C5A—C13A—N1A | −110.4 (3) | C21B—N1B—C13B—C5B | 54.5 (4) |
C21A—N1A—C14A—O1A | 177.5 (3) | C14B—N1B—C13B—C5B | −128.2 (3) |
C13A—N1A—C14A—O1A | 3.0 (5) | C6B—C5B—C13B—N1B | −113.3 (3) |
C21A—N1A—C14A—C15A | −3.3 (4) | C4B—C5B—C13B—N1B | 70.1 (4) |
C13A—N1A—C14A—C15A | −177.8 (3) | C21B—N1B—C14B—O1B | 178.8 (3) |
O1A—C14A—C15A—C20A | −179.5 (4) | C13B—N1B—C14B—O1B | 1.2 (5) |
N1A—C14A—C15A—C20A | 1.3 (4) | C21B—N1B—C14B—C15B | −2.2 (4) |
O1A—C14A—C15A—C16A | 2.2 (6) | C13B—N1B—C14B—C15B | −179.8 (3) |
N1A—C14A—C15A—C16A | −176.9 (3) | O1B—C14B—C15B—C16B | 0.6 (6) |
C20A—C15A—C16A—C17A | −1.6 (5) | N1B—C14B—C15B—C16B | −178.4 (3) |
C14A—C15A—C16A—C17A | 176.5 (3) | O1B—C14B—C15B—C20B | −180.0 (4) |
C15A—C16A—C17A—C18A | 0.8 (6) | N1B—C14B—C15B—C20B | 1.1 (4) |
C16A—C17A—C18A—C19A | 0.4 (6) | C20B—C15B—C16B—C17B | 0.3 (5) |
C17A—C18A—C19A—C20A | −0.8 (6) | C14B—C15B—C16B—C17B | 179.7 (3) |
C16A—C15A—C20A—C19A | 1.3 (5) | C15B—C16B—C17B—C18B | −0.1 (6) |
C14A—C15A—C20A—C19A | −177.2 (3) | C16B—C17B—C18B—C19B | 0.0 (6) |
C16A—C15A—C20A—C21A | 179.4 (3) | C17B—C18B—C19B—C20B | 0.0 (6) |
C14A—C15A—C20A—C21A | 0.9 (4) | C18B—C19B—C20B—C15B | 0.2 (5) |
C18A—C19A—C20A—C15A | 0.0 (6) | C18B—C19B—C20B—C21B | 180.0 (3) |
C18A—C19A—C20A—C21A | −177.7 (4) | C16B—C15B—C20B—C19B | −0.4 (5) |
C14A—N1A—C21A—O2A | −176.4 (3) | C14B—C15B—C20B—C19B | −179.9 (3) |
C13A—N1A—C21A—O2A | −2.0 (6) | C16B—C15B—C20B—C21B | 179.8 (3) |
C14A—N1A—C21A—C20A | 3.9 (4) | C14B—C15B—C20B—C21B | 0.3 (4) |
C13A—N1A—C21A—C20A | 178.3 (3) | C14B—N1B—C21B—O2B | −177.6 (3) |
C15A—C20A—C21A—O2A | 177.4 (4) | C13B—N1B—C21B—O2B | 0.0 (5) |
C19A—C20A—C21A—O2A | −4.6 (7) | C14B—N1B—C21B—C20B | 2.4 (4) |
C15A—C20A—C21A—N1A | −2.9 (4) | C13B—N1B—C21B—C20B | 179.9 (3) |
C19A—C20A—C21A—N1A | 175.0 (4) | C19B—C20B—C21B—O2B | −1.4 (6) |
C1A—C6A—C22A—C23A | 91.4 (4) | C15B—C20B—C21B—O2B | 178.4 (3) |
C5A—C6A—C22A—C23A | −87.1 (4) | C19B—C20B—C21B—N1B | 178.7 (3) |
C6B—C1B—C2B—C3B | 4.1 (4) | C15B—C20B—C21B—N1B | −1.6 (4) |
C7B—C1B—C2B—C3B | −173.0 (3) | C5B—C6B—C22B—C23B | −90.3 (4) |
C6B—C1B—C2B—C8B | −176.7 (3) | C1B—C6B—C22B—C23B | 90.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10A—H10B···O2B | 0.99 | 2.35 | 3.223 (4) | 147 |
C11A—H11A···N1A | 0.99 | 2.54 | 3.283 (4) | 132 |
C13A—H13B···Br2Bi | 0.99 | 2.92 | 3.746 (3) | 142 |
C13A—H13B···O1A | 0.99 | 2.52 | 2.914 (4) | 103 |
C9B—H9F···Br2Aii | 0.98 | 3.00 | 3.921 (4) | 158 |
C11B—H11D···N1B | 0.99 | 2.45 | 3.207 (4) | 133 |
C12B—H12D···Br1Bii | 0.98 | 2.86 | 3.499 (4) | 123 |
C13B—H13D···O1B | 0.99 | 2.53 | 2.928 (4) | 104 |
C22B—H22D···O2B | 0.99 | 2.64 | 3.322 (4) | 126 |
C23B—H23E···O2Aiii | 0.98 | 2.43 | 3.226 (5) | 138 |
C22A—H22B···O2A | 0.99 | 2.59 | 3.278 (4) | 126 |
C9B—H9D···Cg4iv | 0.98 | 2.96 | 3.731 (5) | 137 |
C23B—H23D···Cg4v | 0.98 | 2.92 | 3.542 (5) | 122 |
C12C—H12I···N1B | 0.98 | 2.56 | 3.24 (2) | 126 |
Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) x+1/2, −y+1/2, z−1/2. |
C31H29BrN2O4 | F(000) = 1184 |
Mr = 573.47 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.899 (2) Å | Cell parameters from 3744 reflections |
b = 12.9748 (15) Å | θ = 2.0–22.5° |
c = 16.763 (3) Å | µ = 1.59 mm−1 |
β = 109.168 (13)° | T = 153 K |
V = 2649.9 (7) Å3 | Piece, colorless |
Z = 4 | 0.18 × 0.18 × 0.15 mm |
STOE IPDS 2 diffractometer | 4941 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3442 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.115 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.5°, θmin = 1.7° |
rotation method scans | h = −15→15 |
Absorption correction: integration | k = −15→15 |
Tmin = 0.695, Tmax = 0.844 | l = −19→20 |
26391 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0406P)2 + 4.7828P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
4941 reflections | Δρmax = 0.38 e Å−3 |
346 parameters | Δρmin = −0.67 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 | ||
Br1 | 0.52316 (4) | 0.01014 (4) | 0.79824 (3) | 0.04165 (17) | |
O1 | 0.0480 (2) | −0.1049 (2) | 0.44957 (19) | 0.0269 (7) | |
O2 | 0.2500 (2) | 0.1152 (2) | 0.34544 (18) | 0.0264 (7) | |
O3 | 0.2841 (3) | 0.5612 (2) | 0.47753 (19) | 0.0337 (7) | |
O4 | 0.4148 (2) | 0.4359 (2) | 0.74727 (17) | 0.0235 (6) | |
N1 | 0.1509 (2) | 0.0228 (2) | 0.4147 (2) | 0.0178 (7) | |
N2 | 0.3553 (3) | 0.4731 (2) | 0.6045 (2) | 0.0187 (7) | |
C1 | 0.4494 (3) | 0.1118 (3) | 0.6341 (3) | 0.0207 (8) | |
C2 | 0.3495 (3) | 0.0700 (3) | 0.5826 (2) | 0.0186 (8) | |
C3 | 0.2686 (3) | 0.1364 (3) | 0.5330 (2) | 0.0169 (8) | |
C4 | 0.2886 (3) | 0.2437 (3) | 0.5314 (2) | 0.0170 (8) | |
C5 | 0.3903 (3) | 0.2834 (3) | 0.5827 (2) | 0.0178 (8) | |
C6 | 0.4692 (3) | 0.2186 (3) | 0.6364 (2) | 0.0183 (8) | |
C7 | 0.5375 (3) | 0.0407 (3) | 0.6872 (3) | 0.0261 (10) | |
H7A | 0.610137 | 0.072469 | 0.695790 | 0.031* | |
H7B | 0.534643 | −0.024818 | 0.656210 | 0.031* | |
C8 | 0.3313 (3) | −0.0454 (3) | 0.5824 (3) | 0.0218 (9) | |
H8A | 0.251482 | −0.059241 | 0.565489 | 0.026* | |
H8B | 0.365684 | −0.072266 | 0.640352 | 0.026* | |
C9 | 0.3788 (4) | −0.1030 (3) | 0.5223 (3) | 0.0303 (10) | |
H9A | 0.347178 | −0.074907 | 0.465118 | 0.046* | |
H9B | 0.360849 | −0.176407 | 0.521898 | 0.046* | |
H9C | 0.458681 | −0.094380 | 0.541444 | 0.046* | |
C10 | 0.1550 (3) | 0.0942 (3) | 0.4834 (2) | 0.0205 (9) | |
H10A | 0.125136 | 0.058587 | 0.523338 | 0.025* | |
H10B | 0.106010 | 0.153176 | 0.459244 | 0.025* | |
C11 | 0.0915 (3) | −0.0691 (3) | 0.4011 (3) | 0.0186 (8) | |
C12 | 0.0940 (3) | −0.1109 (3) | 0.3197 (2) | 0.0189 (8) | |
C13 | 0.0457 (3) | −0.2003 (3) | 0.2775 (3) | 0.0258 (10) | |
H13 | 0.004436 | −0.245548 | 0.300068 | 0.031* | |
C14 | 0.0612 (4) | −0.2193 (3) | 0.2012 (3) | 0.0325 (11) | |
H14 | 0.030282 | −0.279843 | 0.170719 | 0.039* | |
C15 | 0.1209 (4) | −0.1524 (3) | 0.1672 (3) | 0.0324 (11) | |
H15 | 0.129331 | −0.167964 | 0.114331 | 0.039* | |
C16 | 0.1682 (3) | −0.0627 (3) | 0.2106 (3) | 0.0246 (9) | |
H16 | 0.208922 | −0.016774 | 0.188112 | 0.030* | |
C17 | 0.1535 (3) | −0.0438 (3) | 0.2871 (2) | 0.0189 (8) | |
C18 | 0.1925 (3) | 0.0425 (3) | 0.3490 (2) | 0.0179 (8) | |
C19 | 0.2003 (3) | 0.3149 (3) | 0.4773 (3) | 0.0215 (9) | |
H19A | 0.161193 | 0.280095 | 0.423207 | 0.026* | |
H19B | 0.235232 | 0.377749 | 0.464336 | 0.026* | |
C20 | 0.1163 (3) | 0.3462 (3) | 0.5208 (3) | 0.0283 (10) | |
H20A | 0.062288 | 0.393705 | 0.484201 | 0.042* | |
H20B | 0.154562 | 0.380291 | 0.574660 | 0.042* | |
H20C | 0.078697 | 0.284601 | 0.531248 | 0.042* | |
C21 | 0.4188 (3) | 0.3966 (3) | 0.5753 (3) | 0.0202 (9) | |
H21A | 0.497534 | 0.406640 | 0.607674 | 0.024* | |
H21B | 0.409090 | 0.411132 | 0.515254 | 0.024* | |
C22 | 0.2951 (3) | 0.5522 (3) | 0.5513 (3) | 0.0246 (9) | |
C23 | 0.2531 (3) | 0.6184 (3) | 0.6061 (3) | 0.0219 (9) | |
C24 | 0.1883 (4) | 0.7063 (3) | 0.5864 (3) | 0.0308 (10) | |
H24 | 0.160892 | 0.732223 | 0.530356 | 0.037* | |
C25 | 0.1652 (4) | 0.7548 (3) | 0.6535 (3) | 0.0335 (11) | |
H25 | 0.119858 | 0.814329 | 0.642455 | 0.040* | |
C26 | 0.2069 (4) | 0.7180 (3) | 0.7352 (3) | 0.0373 (12) | |
H26 | 0.191087 | 0.753832 | 0.779323 | 0.045* | |
C27 | 0.2714 (4) | 0.6298 (3) | 0.7542 (3) | 0.0284 (10) | |
H27 | 0.299597 | 0.604064 | 0.810256 | 0.034* | |
C28 | 0.2928 (3) | 0.5812 (3) | 0.6878 (3) | 0.0227 (9) | |
C29 | 0.3610 (3) | 0.4885 (3) | 0.6876 (2) | 0.0194 (8) | |
C30 | 0.5750 (3) | 0.2621 (3) | 0.6972 (3) | 0.0208 (9) | |
H30A | 0.601244 | 0.216141 | 0.746913 | 0.025* | |
H30B | 0.559601 | 0.330376 | 0.717248 | 0.025* | |
C31 | 0.6659 (3) | 0.2740 (3) | 0.6580 (3) | 0.0257 (9) | |
H31A | 0.686331 | 0.205933 | 0.642623 | 0.039* | |
H31B | 0.730070 | 0.306456 | 0.698949 | 0.039* | |
H31C | 0.639585 | 0.317153 | 0.607382 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0519 (3) | 0.0366 (3) | 0.0270 (2) | 0.0005 (2) | 0.0001 (2) | 0.0070 (2) |
O1 | 0.0267 (15) | 0.0224 (15) | 0.0341 (17) | −0.0046 (13) | 0.0132 (14) | −0.0026 (13) |
O2 | 0.0301 (16) | 0.0216 (15) | 0.0251 (16) | −0.0051 (13) | 0.0057 (13) | 0.0031 (12) |
O3 | 0.054 (2) | 0.0249 (16) | 0.0203 (17) | 0.0032 (15) | 0.0104 (15) | 0.0044 (12) |
O4 | 0.0284 (15) | 0.0184 (14) | 0.0218 (15) | 0.0000 (12) | 0.0054 (13) | 0.0021 (12) |
N1 | 0.0131 (15) | 0.0174 (16) | 0.0216 (17) | −0.0032 (13) | 0.0040 (13) | −0.0006 (13) |
N2 | 0.0244 (17) | 0.0112 (15) | 0.0202 (17) | 0.0039 (13) | 0.0070 (14) | 0.0002 (13) |
C1 | 0.021 (2) | 0.0183 (19) | 0.022 (2) | 0.0021 (16) | 0.0072 (17) | −0.0005 (16) |
C2 | 0.0200 (19) | 0.0159 (19) | 0.021 (2) | −0.0025 (16) | 0.0078 (17) | −0.0030 (15) |
C3 | 0.0160 (19) | 0.0176 (19) | 0.0160 (19) | −0.0026 (15) | 0.0038 (16) | −0.0032 (15) |
C4 | 0.0193 (19) | 0.0186 (19) | 0.0132 (19) | 0.0020 (16) | 0.0054 (15) | −0.0022 (15) |
C5 | 0.021 (2) | 0.0120 (18) | 0.021 (2) | 0.0005 (15) | 0.0064 (17) | −0.0021 (15) |
C6 | 0.0181 (19) | 0.0155 (18) | 0.021 (2) | −0.0039 (15) | 0.0059 (16) | −0.0028 (16) |
C7 | 0.026 (2) | 0.020 (2) | 0.026 (2) | 0.0007 (17) | 0.0008 (18) | −0.0013 (17) |
C8 | 0.024 (2) | 0.0161 (18) | 0.022 (2) | −0.0031 (16) | 0.0028 (18) | 0.0011 (15) |
C9 | 0.038 (3) | 0.018 (2) | 0.030 (2) | 0.0044 (19) | 0.005 (2) | −0.0017 (18) |
C10 | 0.0176 (19) | 0.020 (2) | 0.021 (2) | 0.0004 (16) | 0.0023 (17) | −0.0056 (16) |
C11 | 0.0125 (18) | 0.0164 (19) | 0.024 (2) | 0.0012 (15) | 0.0021 (17) | 0.0038 (16) |
C12 | 0.0157 (19) | 0.0167 (19) | 0.023 (2) | 0.0033 (16) | 0.0042 (16) | −0.0019 (16) |
C13 | 0.022 (2) | 0.0162 (19) | 0.035 (3) | −0.0004 (16) | 0.0039 (19) | −0.0028 (17) |
C14 | 0.032 (2) | 0.025 (2) | 0.033 (3) | 0.0010 (19) | 0.000 (2) | −0.0104 (19) |
C15 | 0.040 (3) | 0.031 (2) | 0.022 (2) | 0.007 (2) | 0.004 (2) | −0.0060 (19) |
C16 | 0.024 (2) | 0.027 (2) | 0.019 (2) | 0.0048 (17) | 0.0015 (17) | 0.0058 (17) |
C17 | 0.0156 (19) | 0.0180 (19) | 0.019 (2) | 0.0040 (15) | −0.0001 (16) | 0.0032 (15) |
C18 | 0.0160 (19) | 0.0159 (19) | 0.018 (2) | 0.0032 (15) | −0.0002 (16) | 0.0034 (15) |
C19 | 0.022 (2) | 0.0172 (19) | 0.023 (2) | −0.0003 (16) | 0.0041 (17) | 0.0011 (16) |
C20 | 0.023 (2) | 0.022 (2) | 0.038 (3) | 0.0052 (18) | 0.007 (2) | 0.0009 (19) |
C21 | 0.025 (2) | 0.0137 (18) | 0.021 (2) | −0.0018 (16) | 0.0063 (17) | −0.0041 (15) |
C22 | 0.026 (2) | 0.0132 (19) | 0.033 (3) | −0.0029 (17) | 0.0073 (19) | −0.0015 (17) |
C23 | 0.022 (2) | 0.0153 (19) | 0.027 (2) | −0.0029 (16) | 0.0066 (18) | −0.0007 (16) |
C24 | 0.033 (2) | 0.019 (2) | 0.040 (3) | 0.0007 (18) | 0.012 (2) | 0.0022 (19) |
C25 | 0.030 (2) | 0.017 (2) | 0.057 (3) | 0.0038 (18) | 0.020 (2) | −0.003 (2) |
C26 | 0.038 (3) | 0.030 (2) | 0.053 (3) | 0.001 (2) | 0.027 (2) | −0.008 (2) |
C27 | 0.033 (2) | 0.027 (2) | 0.031 (2) | −0.0021 (19) | 0.017 (2) | −0.0028 (19) |
C28 | 0.024 (2) | 0.0156 (18) | 0.030 (2) | −0.0036 (16) | 0.0101 (18) | −0.0024 (17) |
C29 | 0.0222 (19) | 0.0147 (18) | 0.022 (2) | −0.0061 (16) | 0.0087 (16) | −0.0017 (17) |
C30 | 0.019 (2) | 0.0180 (19) | 0.021 (2) | −0.0012 (16) | 0.0007 (17) | −0.0048 (16) |
C31 | 0.024 (2) | 0.019 (2) | 0.033 (2) | 0.0019 (17) | 0.0073 (19) | −0.0040 (17) |
Br1—C7 | 1.970 (4) | C13—C14 | 1.381 (6) |
O1—C11 | 1.221 (5) | C13—H13 | 0.9500 |
O2—C18 | 1.213 (5) | C14—C15 | 1.399 (7) |
O3—C22 | 1.204 (5) | C14—H14 | 0.9500 |
O4—C29 | 1.222 (5) | C15—C16 | 1.401 (6) |
N1—C11 | 1.395 (5) | C15—H15 | 0.9500 |
N1—C18 | 1.399 (5) | C16—C17 | 1.380 (6) |
N1—C10 | 1.465 (5) | C16—H16 | 0.9500 |
N2—C29 | 1.384 (5) | C17—C18 | 1.497 (5) |
N2—C22 | 1.413 (5) | C19—C20 | 1.547 (6) |
N2—C21 | 1.471 (5) | C19—H19A | 0.9900 |
C1—C2 | 1.403 (5) | C19—H19B | 0.9900 |
C1—C6 | 1.407 (5) | C20—H20A | 0.9800 |
C1—C7 | 1.507 (5) | C20—H20B | 0.9800 |
C2—C3 | 1.397 (5) | C20—H20C | 0.9800 |
C2—C8 | 1.515 (5) | C21—H21A | 0.9900 |
C3—C4 | 1.418 (5) | C21—H21B | 0.9900 |
C3—C10 | 1.529 (5) | C22—C23 | 1.483 (6) |
C4—C5 | 1.409 (5) | C23—C28 | 1.383 (6) |
C4—C19 | 1.515 (5) | C23—C24 | 1.388 (6) |
C5—C6 | 1.396 (5) | C24—C25 | 1.403 (7) |
C5—C21 | 1.530 (5) | C24—H24 | 0.9500 |
C6—C30 | 1.519 (5) | C25—C26 | 1.382 (7) |
C7—H7A | 0.9900 | C25—H25 | 0.9500 |
C7—H7B | 0.9900 | C26—C27 | 1.389 (6) |
C8—C9 | 1.534 (6) | C26—H26 | 0.9500 |
C8—H8A | 0.9900 | C27—C28 | 1.383 (6) |
C8—H8B | 0.9900 | C27—H27 | 0.9500 |
C9—H9A | 0.9800 | C28—C29 | 1.491 (5) |
C9—H9B | 0.9800 | C30—C31 | 1.528 (6) |
C9—H9C | 0.9800 | C30—H30A | 0.9900 |
C10—H10A | 0.9900 | C30—H30B | 0.9900 |
C10—H10B | 0.9900 | C31—H31A | 0.9800 |
C11—C12 | 1.478 (6) | C31—H31B | 0.9800 |
C12—C17 | 1.386 (6) | C31—H31C | 0.9800 |
C12—C13 | 1.394 (5) | ||
C11—N1—C18 | 111.1 (3) | C17—C16—C15 | 117.4 (4) |
C11—N1—C10 | 123.1 (3) | C17—C16—H16 | 121.3 |
C18—N1—C10 | 125.4 (3) | C15—C16—H16 | 121.3 |
C29—N2—C22 | 111.5 (3) | C16—C17—C12 | 121.2 (4) |
C29—N2—C21 | 125.6 (3) | C16—C17—C18 | 131.3 (4) |
C22—N2—C21 | 122.0 (3) | C12—C17—C18 | 107.5 (3) |
C2—C1—C6 | 121.3 (3) | O2—C18—N1 | 125.4 (4) |
C2—C1—C7 | 119.3 (3) | O2—C18—C17 | 128.3 (4) |
C6—C1—C7 | 119.5 (3) | N1—C18—C17 | 106.3 (3) |
C3—C2—C1 | 118.9 (3) | C4—C19—C20 | 112.6 (3) |
C3—C2—C8 | 121.5 (3) | C4—C19—H19A | 109.1 |
C1—C2—C8 | 119.6 (4) | C20—C19—H19A | 109.1 |
C2—C3—C4 | 120.8 (3) | C4—C19—H19B | 109.1 |
C2—C3—C10 | 119.9 (3) | C20—C19—H19B | 109.1 |
C4—C3—C10 | 119.3 (3) | H19A—C19—H19B | 107.8 |
C5—C4—C3 | 119.1 (3) | C19—C20—H20A | 109.5 |
C5—C4—C19 | 120.6 (3) | C19—C20—H20B | 109.5 |
C3—C4—C19 | 120.3 (3) | H20A—C20—H20B | 109.5 |
C6—C5—C4 | 120.6 (3) | C19—C20—H20C | 109.5 |
C6—C5—C21 | 119.1 (3) | H20A—C20—H20C | 109.5 |
C4—C5—C21 | 120.1 (3) | H20B—C20—H20C | 109.5 |
C5—C6—C1 | 119.2 (3) | N2—C21—C5 | 116.5 (3) |
C5—C6—C30 | 120.8 (3) | N2—C21—H21A | 108.2 |
C1—C6—C30 | 120.0 (3) | C5—C21—H21A | 108.2 |
C1—C7—Br1 | 113.3 (3) | N2—C21—H21B | 108.2 |
C1—C7—H7A | 108.9 | C5—C21—H21B | 108.2 |
Br1—C7—H7A | 108.9 | H21A—C21—H21B | 107.3 |
C1—C7—H7B | 108.9 | O3—C22—N2 | 125.0 (4) |
Br1—C7—H7B | 108.9 | O3—C22—C23 | 129.5 (4) |
H7A—C7—H7B | 107.7 | N2—C22—C23 | 105.5 (4) |
C2—C8—C9 | 112.8 (3) | C28—C23—C24 | 121.3 (4) |
C2—C8—H8A | 109.0 | C28—C23—C22 | 108.7 (3) |
C9—C8—H8A | 109.0 | C24—C23—C22 | 130.0 (4) |
C2—C8—H8B | 109.0 | C23—C24—C25 | 116.6 (4) |
C9—C8—H8B | 109.0 | C23—C24—H24 | 121.7 |
H8A—C8—H8B | 107.8 | C25—C24—H24 | 121.7 |
C8—C9—H9A | 109.5 | C26—C25—C24 | 121.6 (4) |
C8—C9—H9B | 109.5 | C26—C25—H25 | 119.2 |
H9A—C9—H9B | 109.5 | C24—C25—H25 | 119.2 |
C8—C9—H9C | 109.5 | C25—C26—C27 | 121.3 (4) |
H9A—C9—H9C | 109.5 | C25—C26—H26 | 119.3 |
H9B—C9—H9C | 109.5 | C27—C26—H26 | 119.3 |
N1—C10—C3 | 115.7 (3) | C28—C27—C26 | 117.0 (4) |
N1—C10—H10A | 108.3 | C28—C27—H27 | 121.5 |
C3—C10—H10A | 108.3 | C26—C27—H27 | 121.5 |
N1—C10—H10B | 108.3 | C23—C28—C27 | 122.1 (4) |
C3—C10—H10B | 108.3 | C23—C28—C29 | 107.8 (4) |
H10A—C10—H10B | 107.4 | C27—C28—C29 | 130.1 (4) |
O1—C11—N1 | 124.3 (4) | O4—C29—N2 | 124.9 (4) |
O1—C11—C12 | 129.0 (3) | O4—C29—C28 | 128.7 (4) |
N1—C11—C12 | 106.7 (3) | N2—C29—C28 | 106.4 (3) |
C17—C12—C13 | 122.4 (4) | C6—C30—C31 | 113.3 (3) |
C17—C12—C11 | 108.4 (3) | C6—C30—H30A | 108.9 |
C13—C12—C11 | 129.2 (4) | C31—C30—H30A | 108.9 |
C14—C13—C12 | 116.2 (4) | C6—C30—H30B | 108.9 |
C14—C13—H13 | 121.9 | C31—C30—H30B | 108.9 |
C12—C13—H13 | 121.9 | H30A—C30—H30B | 107.7 |
C13—C14—C15 | 122.2 (4) | C30—C31—H31A | 109.5 |
C13—C14—H14 | 118.9 | C30—C31—H31B | 109.5 |
C15—C14—H14 | 118.9 | H31A—C31—H31B | 109.5 |
C14—C15—C16 | 120.6 (4) | C30—C31—H31C | 109.5 |
C14—C15—H15 | 119.7 | H31A—C31—H31C | 109.5 |
C16—C15—H15 | 119.7 | H31B—C31—H31C | 109.5 |
C6—C1—C2—C3 | −0.1 (6) | C13—C12—C17—C16 | −0.3 (6) |
C7—C1—C2—C3 | −179.5 (4) | C11—C12—C17—C16 | −179.1 (3) |
C6—C1—C2—C8 | −179.6 (4) | C13—C12—C17—C18 | 179.9 (3) |
C7—C1—C2—C8 | 1.0 (6) | C11—C12—C17—C18 | 1.1 (4) |
C1—C2—C3—C4 | 3.0 (6) | C11—N1—C18—O2 | −177.6 (3) |
C8—C2—C3—C4 | −177.5 (4) | C10—N1—C18—O2 | 10.3 (6) |
C1—C2—C3—C10 | −173.8 (4) | C11—N1—C18—C17 | 1.3 (4) |
C8—C2—C3—C10 | 5.8 (6) | C10—N1—C18—C17 | −170.8 (3) |
C2—C3—C4—C5 | −2.1 (6) | C16—C17—C18—O2 | −2.3 (7) |
C10—C3—C4—C5 | 174.7 (4) | C12—C17—C18—O2 | 177.4 (4) |
C2—C3—C4—C19 | 179.9 (4) | C16—C17—C18—N1 | 178.8 (4) |
C10—C3—C4—C19 | −3.3 (6) | C12—C17—C18—N1 | −1.5 (4) |
C3—C4—C5—C6 | −1.9 (6) | C5—C4—C19—C20 | −95.5 (4) |
C19—C4—C5—C6 | 176.1 (4) | C3—C4—C19—C20 | 82.5 (4) |
C3—C4—C5—C21 | 173.4 (3) | C29—N2—C21—C5 | 68.4 (5) |
C19—C4—C5—C21 | −8.6 (6) | C22—N2—C21—C5 | −123.2 (4) |
C4—C5—C6—C1 | 4.7 (6) | C6—C5—C21—N2 | −116.0 (4) |
C21—C5—C6—C1 | −170.6 (4) | C4—C5—C21—N2 | 68.6 (5) |
C4—C5—C6—C30 | −174.8 (4) | C29—N2—C22—O3 | 174.7 (4) |
C21—C5—C6—C30 | 9.8 (6) | C21—N2—C22—O3 | 4.8 (6) |
C2—C1—C6—C5 | −3.8 (6) | C29—N2—C22—C23 | −4.4 (4) |
C7—C1—C6—C5 | 175.6 (4) | C21—N2—C22—C23 | −174.2 (3) |
C2—C1—C6—C30 | 175.8 (4) | O3—C22—C23—C28 | −176.0 (4) |
C7—C1—C6—C30 | −4.8 (6) | N2—C22—C23—C28 | 2.9 (4) |
C2—C1—C7—Br1 | −87.0 (4) | O3—C22—C23—C24 | 1.7 (7) |
C6—C1—C7—Br1 | 93.6 (4) | N2—C22—C23—C24 | −179.3 (4) |
C3—C2—C8—C9 | 96.5 (5) | C28—C23—C24—C25 | −0.1 (6) |
C1—C2—C8—C9 | −84.0 (5) | C22—C23—C24—C25 | −177.6 (4) |
C11—N1—C10—C3 | 135.1 (4) | C23—C24—C25—C26 | 1.3 (6) |
C18—N1—C10—C3 | −53.7 (5) | C24—C25—C26—C27 | −1.6 (7) |
C2—C3—C10—N1 | −66.4 (5) | C25—C26—C27—C28 | 0.6 (7) |
C4—C3—C10—N1 | 116.7 (4) | C24—C23—C28—C27 | −0.9 (6) |
C18—N1—C11—O1 | 178.9 (3) | C22—C23—C28—C27 | 177.1 (4) |
C10—N1—C11—O1 | −8.8 (5) | C24—C23—C28—C29 | −178.6 (4) |
C18—N1—C11—C12 | −0.7 (4) | C22—C23—C28—C29 | −0.6 (4) |
C10—N1—C11—C12 | 171.6 (3) | C26—C27—C28—C23 | 0.6 (6) |
O1—C11—C12—C17 | −179.8 (4) | C26—C27—C28—C29 | 177.8 (4) |
N1—C11—C12—C17 | −0.3 (4) | C22—N2—C29—O4 | −174.3 (4) |
O1—C11—C12—C13 | 1.4 (7) | C21—N2—C29—O4 | −4.9 (6) |
N1—C11—C12—C13 | −179.1 (4) | C22—N2—C29—C28 | 4.0 (4) |
C17—C12—C13—C14 | 0.6 (6) | C21—N2—C29—C28 | 173.5 (3) |
C11—C12—C13—C14 | 179.3 (4) | C23—C28—C29—O4 | 176.3 (4) |
C12—C13—C14—C15 | −0.7 (6) | C27—C28—C29—O4 | −1.3 (7) |
C13—C14—C15—C16 | 0.4 (7) | C23—C28—C29—N2 | −2.0 (4) |
C14—C15—C16—C17 | 0.0 (6) | C27—C28—C29—N2 | −179.5 (4) |
C15—C16—C17—C12 | −0.1 (6) | C5—C6—C30—C31 | −87.0 (5) |
C15—C16—C17—C18 | 179.7 (4) | C1—C6—C30—C31 | 93.4 (5) |
Cg1 and Cg3 are the centroids of the C1–C6 and C12–C17 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O1 | 0.99 | 2.49 | 2.896 (5) | 104 |
C10—H10A···O1i | 0.99 | 2.49 | 3.173 (5) | 126 |
C19—H19B···O3 | 0.99 | 2.45 | 3.373 (5) | 154 |
C21—H21B···O3 | 0.99 | 2.47 | 2.897 (5) | 105 |
C25—H25···O4ii | 0.95 | 2.58 | 3.237 (5) | 127 |
C30—H30B···O4 | 0.99 | 2.50 | 3.346 (5) | 144 |
C31—H31B···O2iii | 0.98 | 2.59 | 3.298 (5) | 129 |
C31—H31C···O3iv | 0.98 | 2.53 | 3.334 (5) | 139 |
C26—H26···Cg1ii | 0.95 | 2.84 | 3.529 (5) | 130 |
C31—H31A···Cg3v | 0.98 | 2.88 | 3.394 (5) | 113 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y, −z+1. |
C—X···Y—C | symmetry code | C—X/Y | X···Y | C—X/Y···Y/X |
C10B—Br2B···O1A—C14A | 1 + x, y, z | 1.980 (3)/1.210 (4) | 3.220 (3) | 129.0 (2)/171.35 (11) |
Funding information
Open-access funding by the Publication Fund of the TU Bergakademie Freiberg is gratefully acknowledged.
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