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d][1,3]dioxol-5-yl)ethyl]-1-(phenylsulfonyl)-1H-indole chloroform 0.585-solvate
and Hirshfeld surface analysis of 3-(bromomethyl)-2-[1,2-dibromo-2-(6-nitrobenzo[aCAS in Crystallography and Biophysics, University of Madras, Chennai, India, and bDepartment of Organic Chemistry, University of Madras, Chennai, India
*Correspondence e-mail: achyuta11@gmail.com
The title indole derivative, C24H17Br3N2O6S, crystallizes with a partial occupancy [0.585 (4)] CHCl3 solvent molecule. The dihedral angles between the indole ring system and pendant nitrobenzodioxolane rings system and phenylsulfonyl ring are 4.81 (14) and 72.24 (19)°, respectively. In the crystal, the indole molecules are linked to each other and to the chloroform molecule by weak C—H⋯O, C—H⋯Cl, C—H⋯π, C—Br⋯π and C—Cl⋯π and aromatic π–π stacking interactions. A Hirshfeld surface analysis was carried out and the intermolecular contacts with the most significant contributions are H⋯O/O⋯H (24.3%), H⋯H (18.4%), Br⋯H/H⋯Br (16.8%) and C⋯H/H⋯C (8.4%).
Keywords: crystal structure; synthesis; 1-(phenylsulfonyl)-1H-indole; Y—X⋯π interactions; hydrogen bonding; Hirshfeld surface analysis.
CCDC reference: 2279852
1. Chemical context
Derivatives of indole have been reported to exhibit antibacterial (Okabe & Adachi, 1998) and antitumour (Schollmeyer et al., 1995
) activities. N-Substituted indole derivatives have been found to exhibit antioxidant properties (Ölgen & Çoban, 2003
, 2002
) and halogenated indole derivatives have demonstrated antibacterial and antifungal activity (Piscopo et al., 1990
). Derivatives of 1-(phenylsulfonyl)indole have proven their usefulness in the synthesis of biologically active and their related analogues, including pyridocarbazoles, such as the anticancer alkaloid ellipticine, carbazoles, furoindoles, pyrroloindoles, indolocarbazoles and other substituted indoles. The indole phenylsulfonyl moiety acts as both a protecting and activating group (Jasinski et al., 2009
). The phenylsulfonyl indole compounds have been shown to inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993
). As part of our studies in this area, we now describe the synthesis and structure of the title molecule C24H17Br3N2O6S·0.585CHCl3, which crystallized as a chloroform solvate.
2. Structural commentary
The C9–C14 phenyl ring makes a dihedral angle of 72.24 (19)° with the C1–C8/N1 indole ring system (Fig. 1). The C1—C15—C16—C17 torsion angle is 175.8 (3)°. The five-member dioxolane ring (C19/C20/O4/C23/O3) adopts an (C23 is displaced from the plane) with pseudo rotation parameters P = 59.3 (17)° and τ = 10.9 (3)°, which are confirmed by the Cremer–Pople puckering parameters Q = 0.097 (5) Å and φ = 329 (3)°. The C1—N1 and C4—N1 bond lengths are 1.423 (5) and 1.427 (5) Å, respectively, while in the case of N atoms in planar configurations, the reported mean value is 1.355 (14) Å (Allen et al., 1987
). This difference is due to the electron-withdrawing nature of the phenylsulfonyl group attached to N1 and has been reported earlier (Palani et al., 2006
). During the synthesis of the title compound, bromination of the methyl group and the double bond between C15 and C16 of the 6-nitrobenzo[d][1,3]dioxol-5-yl)vinyl moiety occurs due to an with Br2. The Br1—C16—C15—Br2 grouping is in a trans configuration and the torsion angle has a value of 178.14 (17)°. Intramolecular C5—H5⋯O1, C15—H15⋯O2, C16—H16⋯O6 and C24—H24B⋯Br2 interactions (Fig. 1
, Table 1
) are observed.
|
![]() | Figure 1 The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level with intramolecular hydrogen bonds shown in light blue. |
3. Supramolecular features
The extended structure exhibits weak intermolecular hydrogen bonds including indole-to-indole C—H⋯O, indole-to-chloroform C—H⋯Cl and chloroform-to-indole C—H⋯O contacts (Fig. 2, Table 1
). The crystal also features C—H⋯π, C—Br⋯π and C—Cl⋯π interactions. The C23—H23⋯Cg2i [symmetry code: (i) x – 1, y, z) interaction where Cg2 is the centroid of the ring C1–C4/N1 has an H⋯Cg2 separation of 2.94 Å with the C—H⋯Cg angle being 117°. In the case of the C—Br⋯π interaction, the C16—Br1⋯ Cg4 (Cg4 is the centroid of the C9–C14 ring) interaction has a Br⋯Cg4 distance of 3.691 (2) Å with the C—Br⋯Cg angle being 111.46 (11) °. The C1—Cl2⋯ Cg4 interaction to the other face of the C9–C14 ring has a Cl⋯Cg distance of 3.236 (4) Å with the C—Cl⋯Cg angle being 167 (5)°.
![]() | Figure 2 The crystal packing of the title compound viewed along the a-axis direction. |
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.43, update of November 2022; Groom et al., 2016) for the 3-methyl-1-(phenylsulfonyl)-1H-indole skeleton gave four hits. The structures of 2-azidomethyl-3-methyl-1-phenylsulfonyl-1H-indole (CSD refcode AYOSIR; Karthikeyan et al., 2011
), 2-chloromethyl-3-methyl-1-phenylsulfonyl-1H-indole (FUGRUV; Saravanan et al., 2009
) and (E)-2-(4-methoxystyryl)-3-methyl-1-phenylsulfonyl-1H-indole (NUPTUP; Umadevi et al., 2015
) have additional groups attached to the 3-methyl-1-phenylsulfonyl-1H-indole core. Conversely, 2-(2-{1,4-dimethyl-2-[3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl]cyclohex-3-en-1-yl}vinyl)-3-methyl-1-(phenylsulfonyl)-1H-indole tetrahydrate (FOLGOE; Dethe et al., 2014
) consists of two 3-methyl-1-(phenylsulfonyl)-1H-indole groups. The search fragment 3-bromomethyl-1-phenylsulfonyl-1H-indole yielded one hit, 3-bromomethyl-1-phenylsulfonyl-1H-indole-2-carbonitrile (TECGEO; Palani et al., 2006
).
5. Hirshfeld surface analysis
The Hirshfeld surface analysis and the associated two-dimensional fingerprint plots were determined using the Crystal Explorer 21 software (Spackman et al., 2021). Fig. 3
shows the Hirshfeld surface mapped over dnorm for the title compound, where red denotes shorter contacts, blue longer contacts and the white regions indicate contacts around the van der Waals separation. The two-dimensional fingerprint plots (Parkin et al., 2007
) detailing the various interactions for the molecule are shown in Fig. 4
. For points on the Hirshfeld surface, di is the distance to the nearest atom inside and de is the distance to the nearest atom outside the surface. The combination of de and di in the form of a two-dimensional fingerprint plot summarizes the intermolecular contacts in the crystal: in the title molecule, the most significant intermolecular contacts are H⋯O/O⋯H (24.3%), H⋯H (18.4%), Br⋯H/H⋯Br (16.8%) and C⋯H/H⋯C (8.4%).
![]() | Figure 3 The Hirshfeld surface of the title compound mapped over dnorm. |
![]() | Figure 4 The fingerprint plots of the title compound delineated into the various labelled contacts. |
6. Synthesis and crystallization
A solution of (E)-3-methyl-2-[2-(6-nitrobenzo[d][1,3]dioxol-5-yl)vinyl]-1-(phenylsulfonyl)-1H-indole (0.80 g, 1.73 mmol) and N-bromosuccinimide (NBS, 0.91 g, 5.19 mmol) in dry CCl4 (100 ml) containing a catalytic amount of azobisisobutyronitrile (AIBN, 50 mg) was refluxed for 2 h. The reaction mixture was cooled to room temperature. Then, the suspended succinimide was filtered off and the filtrate was concentrated in vacuo to obtain the crude product, which upon trituration with methanol (10 ml) gave the title compound as a bright-yellow solid. Yield: 800 mg (88%) m.p. 431–433 K. The synthesized compound was crystallized by slow evaporation using chloroform as solvent.
7. Refinement
Crystal data, data collection and structure . The hydrogen atoms were automatically added using a riding model with appropriate AFIX instructions.
|
Supporting information
CCDC reference: 2279852
https://doi.org/10.1107/S2056989023007120/hb8071sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007120/hb8071Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023007120/hb8071Isup3.cml
Data collection: CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); cell
CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.42.36a (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).C24H17Br3N2O6S·0.585CHCl3 | Z = 2 |
Mr = 771.02 | F(000) = 756 |
Triclinic, P1 | Dx = 1.859 Mg m−3 |
a = 10.0987 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.2744 (4) Å | Cell parameters from 10304 reflections |
c = 12.4842 (5) Å | θ = 3.8–77.3° |
α = 99.448 (3)° | µ = 8.09 mm−1 |
β = 110.701 (3)° | T = 100 K |
γ = 100.696 (3)° | Block, yellow |
V = 1377.27 (9) Å3 | 0.09 × 0.07 × 0.04 mm |
SuperNova, Dual, Cu at home/near, HyPix diffractometer | 5783 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5068 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.058 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 77.8°, θmin = 3.8° |
ω scans | h = −12→12 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2021) | k = −15→15 |
Tmin = 0.679, Tmax = 0.918 | l = −15→15 |
32306 measured reflections |
Refinement on F2 | 15 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0756P)2 + 3.2347P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
5783 reflections | Δρmax = 2.45 e Å−3 |
362 parameters | Δρmin = −1.18 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 | 0.58451 (5) | 0.42132 (3) | 0.59315 (4) | 0.02570 (13) | |
Br2 | 0.73154 (5) | 0.14955 (4) | 0.79206 (4) | 0.02939 (13) | |
Br3 | 1.00762 (5) | 0.56830 (4) | 0.86622 (4) | 0.02920 (13) | |
S1 | 0.68128 (11) | 0.12626 (8) | 0.41364 (8) | 0.0223 (2) | |
O2 | 0.6345 (3) | 0.0430 (2) | 0.4695 (3) | 0.0253 (6) | |
O4 | 0.1132 (3) | 0.1454 (3) | 0.7754 (3) | 0.0330 (7) | |
O1 | 0.7479 (3) | 0.0973 (2) | 0.3329 (3) | 0.0262 (6) | |
O3 | 0.1207 (3) | 0.0964 (3) | 0.5903 (3) | 0.0274 (6) | |
O6 | 0.6713 (3) | 0.4960 (3) | 0.9228 (3) | 0.0280 (6) | |
O5 | 0.6049 (4) | 0.4185 (3) | 1.0457 (3) | 0.0343 (7) | |
N1 | 0.8057 (4) | 0.2367 (3) | 0.5219 (3) | 0.0218 (7) | |
N2 | 0.5943 (4) | 0.4196 (3) | 0.9449 (3) | 0.0252 (7) | |
C20 | 0.2451 (5) | 0.2022 (4) | 0.7782 (4) | 0.0257 (8) | |
C19 | 0.2496 (4) | 0.1717 (3) | 0.6678 (4) | 0.0231 (8) | |
C2 | 0.9429 (5) | 0.3497 (3) | 0.7066 (4) | 0.0229 (8) | |
C9 | 0.5355 (5) | 0.1832 (3) | 0.3452 (4) | 0.0242 (8) | |
C8 | 1.1596 (5) | 0.4418 (4) | 0.6586 (4) | 0.0243 (8) | |
H8 | 1.219006 | 0.487579 | 0.736352 | 0.029* | |
C10 | 0.5593 (5) | 0.2662 (4) | 0.2858 (4) | 0.0272 (8) | |
H10 | 0.651715 | 0.290181 | 0.281265 | 0.033* | |
C24 | 1.0022 (5) | 0.4044 (4) | 0.8361 (4) | 0.0259 (8) | |
H24A | 1.102550 | 0.395934 | 0.874397 | 0.031* | |
H24B | 0.939908 | 0.364847 | 0.871497 | 0.031* | |
C16 | 0.6285 (4) | 0.3342 (3) | 0.7156 (3) | 0.0215 (7) | |
H16 | 0.708992 | 0.384543 | 0.790336 | 0.026* | |
C15 | 0.6810 (5) | 0.2339 (3) | 0.6679 (4) | 0.0221 (8) | |
H15 | 0.598316 | 0.182040 | 0.595478 | 0.027* | |
C21 | 0.3578 (5) | 0.2820 (4) | 0.8701 (4) | 0.0275 (9) | |
H21 | 0.354011 | 0.304239 | 0.945258 | 0.033* | |
C7 | 1.2061 (5) | 0.4458 (4) | 0.5668 (4) | 0.0277 (9) | |
H7 | 1.298673 | 0.494833 | 0.581795 | 0.033* | |
C4 | 0.9377 (4) | 0.3002 (3) | 0.5193 (4) | 0.0227 (8) | |
C3 | 1.0226 (4) | 0.3683 (3) | 0.6332 (4) | 0.0228 (8) | |
C17 | 0.4909 (5) | 0.2960 (3) | 0.7380 (4) | 0.0224 (8) | |
C22 | 0.4805 (5) | 0.3296 (3) | 0.8468 (4) | 0.0232 (8) | |
C18 | 0.3703 (5) | 0.2154 (3) | 0.6456 (4) | 0.0232 (8) | |
H18 | 0.372040 | 0.191755 | 0.569903 | 0.028* | |
C23 | 0.0388 (5) | 0.0681 (4) | 0.6607 (4) | 0.0278 (8) | |
H23A | −0.062233 | 0.075806 | 0.623430 | 0.033* | |
H23B | 0.032817 | −0.011831 | 0.667024 | 0.033* | |
C6 | 1.1179 (5) | 0.3783 (4) | 0.4524 (4) | 0.0272 (9) | |
H6 | 1.151707 | 0.383937 | 0.390962 | 0.033* | |
C1 | 0.8102 (5) | 0.2724 (3) | 0.6378 (4) | 0.0228 (8) | |
C5 | 0.9823 (5) | 0.3031 (4) | 0.4253 (4) | 0.0261 (8) | |
H5 | 0.923686 | 0.256456 | 0.347776 | 0.031* | |
C11 | 0.4463 (6) | 0.3134 (4) | 0.2336 (4) | 0.0345 (10) | |
H11 | 0.460782 | 0.370752 | 0.193161 | 0.041* | |
C14 | 0.4009 (5) | 0.1455 (4) | 0.3522 (4) | 0.0296 (9) | |
H14 | 0.386714 | 0.088451 | 0.393030 | 0.036* | |
C12 | 0.3110 (6) | 0.2768 (4) | 0.2402 (5) | 0.0390 (11) | |
H12 | 0.233581 | 0.309611 | 0.204504 | 0.047* | |
C13 | 0.2885 (6) | 0.1925 (4) | 0.2988 (5) | 0.0397 (11) | |
H13 | 0.195483 | 0.167228 | 0.302029 | 0.048* | |
Cl2 | 0.3028 (5) | 0.0547 (3) | 0.0343 (3) | 0.0840 (13) | 0.585 (4) |
Cl3 | 0.0526 (5) | −0.1122 (4) | −0.1145 (5) | 0.1007 (15) | 0.585 (4) |
Cl1 | 0.3205 (5) | −0.1710 (3) | −0.0639 (3) | 0.0828 (13) | 0.585 (4) |
C1A | 0.247 (2) | −0.0539 (11) | −0.0772 (11) | 0.079 (4) | 0.585 (4) |
H1A | 0.257878 | −0.026390 | −0.145381 | 0.094* | 0.585 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0364 (2) | 0.0205 (2) | 0.0333 (2) | 0.00951 (17) | 0.02579 (19) | 0.01161 (17) |
Br2 | 0.0408 (3) | 0.0259 (2) | 0.0337 (2) | 0.01040 (18) | 0.0248 (2) | 0.01486 (19) |
Br3 | 0.0391 (3) | 0.0254 (2) | 0.0270 (2) | 0.00873 (18) | 0.01907 (19) | 0.00274 (17) |
S1 | 0.0331 (5) | 0.0168 (4) | 0.0233 (4) | 0.0063 (4) | 0.0191 (4) | 0.0041 (4) |
O2 | 0.0382 (16) | 0.0165 (13) | 0.0269 (14) | 0.0053 (11) | 0.0206 (12) | 0.0053 (11) |
O4 | 0.0318 (16) | 0.0381 (18) | 0.0357 (17) | 0.0024 (13) | 0.0237 (14) | 0.0115 (14) |
O1 | 0.0374 (16) | 0.0212 (14) | 0.0280 (14) | 0.0086 (12) | 0.0232 (13) | 0.0034 (12) |
O3 | 0.0298 (14) | 0.0230 (14) | 0.0316 (15) | 0.0018 (11) | 0.0181 (12) | 0.0050 (12) |
O6 | 0.0329 (15) | 0.0240 (14) | 0.0307 (15) | 0.0037 (12) | 0.0210 (13) | 0.0015 (12) |
O5 | 0.0376 (17) | 0.0455 (19) | 0.0226 (15) | 0.0078 (14) | 0.0183 (13) | 0.0051 (14) |
N1 | 0.0297 (17) | 0.0204 (16) | 0.0213 (16) | 0.0050 (13) | 0.0182 (13) | 0.0047 (13) |
N2 | 0.0299 (17) | 0.0273 (18) | 0.0249 (17) | 0.0086 (14) | 0.0183 (14) | 0.0049 (14) |
C20 | 0.028 (2) | 0.027 (2) | 0.034 (2) | 0.0084 (16) | 0.0218 (17) | 0.0130 (17) |
C19 | 0.030 (2) | 0.0172 (18) | 0.0255 (19) | 0.0051 (15) | 0.0158 (16) | 0.0057 (15) |
C2 | 0.031 (2) | 0.0206 (18) | 0.027 (2) | 0.0091 (15) | 0.0207 (17) | 0.0091 (16) |
C9 | 0.035 (2) | 0.0190 (18) | 0.0243 (19) | 0.0096 (16) | 0.0176 (16) | 0.0032 (15) |
C8 | 0.0286 (19) | 0.0233 (19) | 0.027 (2) | 0.0075 (16) | 0.0183 (16) | 0.0058 (16) |
C10 | 0.039 (2) | 0.0204 (19) | 0.030 (2) | 0.0084 (17) | 0.0221 (18) | 0.0064 (17) |
C24 | 0.035 (2) | 0.023 (2) | 0.026 (2) | 0.0053 (16) | 0.0196 (17) | 0.0060 (16) |
C16 | 0.033 (2) | 0.0178 (17) | 0.0229 (18) | 0.0071 (15) | 0.0210 (16) | 0.0050 (15) |
C15 | 0.033 (2) | 0.0175 (18) | 0.0235 (18) | 0.0068 (15) | 0.0199 (16) | 0.0058 (15) |
C21 | 0.036 (2) | 0.031 (2) | 0.026 (2) | 0.0092 (18) | 0.0232 (18) | 0.0101 (17) |
C7 | 0.029 (2) | 0.024 (2) | 0.038 (2) | 0.0053 (16) | 0.0234 (18) | 0.0085 (18) |
C4 | 0.030 (2) | 0.0198 (18) | 0.0259 (19) | 0.0078 (15) | 0.0186 (16) | 0.0075 (15) |
C3 | 0.0298 (19) | 0.0206 (18) | 0.027 (2) | 0.0096 (15) | 0.0193 (16) | 0.0093 (16) |
C17 | 0.033 (2) | 0.0176 (17) | 0.0259 (19) | 0.0069 (15) | 0.0220 (17) | 0.0077 (15) |
C22 | 0.030 (2) | 0.0206 (18) | 0.0259 (19) | 0.0059 (15) | 0.0193 (16) | 0.0066 (16) |
C18 | 0.031 (2) | 0.0198 (18) | 0.0241 (19) | 0.0069 (15) | 0.0184 (16) | 0.0038 (15) |
C23 | 0.030 (2) | 0.023 (2) | 0.035 (2) | 0.0029 (16) | 0.0195 (18) | 0.0078 (17) |
C6 | 0.038 (2) | 0.026 (2) | 0.031 (2) | 0.0103 (17) | 0.0270 (18) | 0.0110 (17) |
C1 | 0.033 (2) | 0.0214 (18) | 0.0226 (19) | 0.0074 (16) | 0.0202 (16) | 0.0074 (15) |
C5 | 0.037 (2) | 0.025 (2) | 0.0251 (19) | 0.0087 (17) | 0.0216 (17) | 0.0070 (16) |
C11 | 0.052 (3) | 0.025 (2) | 0.036 (2) | 0.015 (2) | 0.026 (2) | 0.0113 (19) |
C14 | 0.041 (2) | 0.0208 (19) | 0.035 (2) | 0.0069 (17) | 0.026 (2) | 0.0049 (17) |
C12 | 0.047 (3) | 0.032 (2) | 0.047 (3) | 0.019 (2) | 0.024 (2) | 0.011 (2) |
C13 | 0.038 (2) | 0.036 (3) | 0.057 (3) | 0.013 (2) | 0.030 (2) | 0.013 (2) |
Cl2 | 0.154 (4) | 0.0441 (15) | 0.0602 (18) | 0.0185 (18) | 0.049 (2) | 0.0213 (13) |
Cl3 | 0.079 (2) | 0.103 (3) | 0.124 (4) | 0.015 (2) | 0.039 (2) | 0.051 (3) |
Cl1 | 0.175 (4) | 0.082 (2) | 0.0621 (17) | 0.085 (2) | 0.091 (2) | 0.0492 (16) |
C1A | 0.152 (14) | 0.051 (6) | 0.044 (6) | 0.021 (8) | 0.054 (8) | 0.014 (5) |
Br1—C16 | 1.978 (4) | C16—H16 | 1.0000 |
Br2—C15 | 1.974 (4) | C16—C15 | 1.542 (5) |
Br3—C24 | 1.971 (4) | C16—C17 | 1.519 (5) |
S1—O2 | 1.429 (3) | C15—H15 | 1.0000 |
S1—O1 | 1.430 (3) | C15—C1 | 1.498 (5) |
S1—N1 | 1.676 (3) | C21—H21 | 0.9500 |
S1—C9 | 1.754 (4) | C21—C22 | 1.415 (5) |
O4—C20 | 1.369 (5) | C7—H7 | 0.9500 |
O4—C23 | 1.429 (6) | C7—C6 | 1.399 (6) |
O3—C19 | 1.362 (5) | C4—C3 | 1.392 (6) |
O3—C23 | 1.443 (5) | C4—C5 | 1.401 (5) |
O6—N2 | 1.236 (5) | C17—C22 | 1.399 (5) |
O5—N2 | 1.227 (5) | C17—C18 | 1.406 (6) |
N1—C4 | 1.427 (5) | C18—H18 | 0.9500 |
N1—C1 | 1.423 (5) | C23—H23A | 0.9900 |
N2—C22 | 1.459 (5) | C23—H23B | 0.9900 |
C20—C19 | 1.387 (6) | C6—H6 | 0.9500 |
C20—C21 | 1.365 (6) | C6—C5 | 1.394 (6) |
C19—C18 | 1.376 (5) | C5—H5 | 0.9500 |
C2—C24 | 1.494 (6) | C11—H11 | 0.9500 |
C2—C3 | 1.436 (5) | C11—C12 | 1.392 (7) |
C2—C1 | 1.371 (6) | C14—H14 | 0.9500 |
C9—C10 | 1.389 (6) | C14—C13 | 1.378 (7) |
C9—C14 | 1.390 (6) | C12—H12 | 0.9500 |
C8—H8 | 0.9500 | C12—C13 | 1.392 (7) |
C8—C7 | 1.388 (6) | C13—H13 | 0.9500 |
C8—C3 | 1.400 (6) | Cl2—C1A | 1.609 (12) |
C10—H10 | 0.9500 | Cl3—C1A | 1.815 (18) |
C10—C11 | 1.380 (7) | Cl1—C1A | 1.742 (15) |
C24—H24A | 0.9900 | C1A—H1A | 1.0000 |
C24—H24B | 0.9900 | ||
O2—S1—O1 | 120.07 (17) | C22—C21—H21 | 121.9 |
O2—S1—N1 | 106.78 (17) | C8—C7—H7 | 119.7 |
O2—S1—C9 | 109.47 (19) | C8—C7—C6 | 120.7 (4) |
O1—S1—N1 | 105.88 (17) | C6—C7—H7 | 119.7 |
O1—S1—C9 | 109.04 (19) | C3—C4—N1 | 107.0 (3) |
N1—S1—C9 | 104.44 (18) | C3—C4—C5 | 122.4 (4) |
C20—O4—C23 | 105.7 (3) | C5—C4—N1 | 130.5 (4) |
C19—O3—C23 | 105.4 (3) | C8—C3—C2 | 131.0 (4) |
C4—N1—S1 | 125.3 (3) | C4—C3—C2 | 108.6 (4) |
C1—N1—S1 | 126.2 (3) | C4—C3—C8 | 120.4 (4) |
C1—N1—C4 | 107.8 (3) | C22—C17—C16 | 124.1 (4) |
O6—N2—C22 | 118.8 (3) | C22—C17—C18 | 118.3 (4) |
O5—N2—O6 | 122.9 (4) | C18—C17—C16 | 117.4 (3) |
O5—N2—C22 | 118.2 (3) | C21—C22—N2 | 114.4 (3) |
O4—C20—C19 | 109.9 (4) | C17—C22—N2 | 122.5 (3) |
C21—C20—O4 | 128.3 (4) | C17—C22—C21 | 123.1 (4) |
C21—C20—C19 | 121.7 (4) | C19—C18—C17 | 118.2 (4) |
O3—C19—C20 | 110.1 (3) | C19—C18—H18 | 120.9 |
O3—C19—C18 | 127.6 (4) | C17—C18—H18 | 120.9 |
C18—C19—C20 | 122.3 (4) | O4—C23—O3 | 107.8 (3) |
C3—C2—C24 | 123.9 (4) | O4—C23—H23A | 110.1 |
C1—C2—C24 | 128.1 (3) | O4—C23—H23B | 110.1 |
C1—C2—C3 | 108.0 (4) | O3—C23—H23A | 110.1 |
C10—C9—S1 | 118.3 (3) | O3—C23—H23B | 110.1 |
C10—C9—C14 | 121.9 (4) | H23A—C23—H23B | 108.5 |
C14—C9—S1 | 119.8 (3) | C7—C6—H6 | 118.8 |
C7—C8—H8 | 121.0 | C5—C6—C7 | 122.3 (4) |
C7—C8—C3 | 118.1 (4) | C5—C6—H6 | 118.8 |
C3—C8—H8 | 121.0 | N1—C1—C15 | 122.1 (4) |
C9—C10—H10 | 120.6 | C2—C1—N1 | 108.5 (3) |
C11—C10—C9 | 118.8 (4) | C2—C1—C15 | 129.2 (4) |
C11—C10—H10 | 120.6 | C4—C5—H5 | 122.0 |
Br3—C24—H24A | 109.3 | C6—C5—C4 | 116.0 (4) |
Br3—C24—H24B | 109.3 | C6—C5—H5 | 122.0 |
C2—C24—Br3 | 111.4 (3) | C10—C11—H11 | 120.0 |
C2—C24—H24A | 109.3 | C10—C11—C12 | 119.9 (4) |
C2—C24—H24B | 109.3 | C12—C11—H11 | 120.0 |
H24A—C24—H24B | 108.0 | C9—C14—H14 | 120.6 |
Br1—C16—H16 | 109.5 | C13—C14—C9 | 118.8 (4) |
C15—C16—Br1 | 106.4 (2) | C13—C14—H14 | 120.6 |
C15—C16—H16 | 109.5 | C11—C12—H12 | 119.8 |
C17—C16—Br1 | 108.4 (3) | C13—C12—C11 | 120.5 (5) |
C17—C16—H16 | 109.5 | C13—C12—H12 | 119.8 |
C17—C16—C15 | 113.4 (3) | C14—C13—C12 | 120.1 (5) |
Br2—C15—H15 | 108.9 | C14—C13—H13 | 120.0 |
C16—C15—Br2 | 106.6 (3) | C12—C13—H13 | 120.0 |
C16—C15—H15 | 108.9 | Cl2—C1A—Cl3 | 106.5 (9) |
C1—C15—Br2 | 110.4 (3) | Cl2—C1A—Cl1 | 120.0 (9) |
C1—C15—C16 | 112.9 (3) | Cl2—C1A—H1A | 108.5 |
C1—C15—H15 | 108.9 | Cl3—C1A—H1A | 108.5 |
C20—C21—H21 | 121.9 | Cl1—C1A—Cl3 | 104.4 (7) |
C20—C21—C22 | 116.2 (4) | Cl1—C1A—H1A | 108.5 |
Br1—C16—C15—Br2 | 178.14 (17) | C10—C9—C14—C13 | −0.2 (7) |
Br1—C16—C15—C1 | 56.7 (4) | C10—C11—C12—C13 | −0.3 (8) |
Br1—C16—C17—C22 | −118.0 (4) | C24—C2—C3—C8 | −4.9 (7) |
Br1—C16—C17—C18 | 66.7 (4) | C24—C2—C3—C4 | 177.2 (4) |
Br2—C15—C1—N1 | 119.7 (4) | C24—C2—C1—N1 | −175.3 (4) |
Br2—C15—C1—C2 | −65.5 (5) | C24—C2—C1—C15 | 9.4 (7) |
S1—N1—C4—C3 | −168.6 (3) | C16—C15—C1—N1 | −121.0 (4) |
S1—N1—C4—C5 | 13.3 (6) | C16—C15—C1—C2 | 53.7 (6) |
S1—N1—C1—C2 | 168.0 (3) | C16—C17—C22—N2 | 10.0 (6) |
S1—N1—C1—C15 | −16.3 (6) | C16—C17—C22—C21 | −171.8 (4) |
S1—C9—C10—C11 | −178.7 (3) | C16—C17—C18—C19 | 174.1 (4) |
S1—C9—C14—C13 | 179.3 (4) | C15—C16—C17—C22 | 124.1 (4) |
O2—S1—N1—C4 | 139.8 (3) | C15—C16—C17—C18 | −51.3 (5) |
O2—S1—N1—C1 | −30.3 (4) | C21—C20—C19—O3 | −176.2 (4) |
O2—S1—C9—C10 | 179.9 (3) | C21—C20—C19—C18 | 3.4 (7) |
O2—S1—C9—C14 | 0.4 (4) | C7—C8—C3—C2 | −176.6 (4) |
O4—C20—C19—O3 | 1.0 (5) | C7—C8—C3—C4 | 1.1 (6) |
O4—C20—C19—C18 | −179.4 (4) | C7—C6—C5—C4 | 1.1 (6) |
O4—C20—C21—C22 | −178.1 (4) | C4—N1—C1—C2 | −3.5 (4) |
O1—S1—N1—C4 | 10.7 (4) | C4—N1—C1—C15 | 172.2 (4) |
O1—S1—N1—C1 | −159.3 (3) | C3—C2—C24—Br3 | 73.2 (5) |
O1—S1—C9—C10 | −47.0 (4) | C3—C2—C1—N1 | 2.6 (5) |
O1—S1—C9—C14 | 133.6 (3) | C3—C2—C1—C15 | −172.7 (4) |
O3—C19—C18—C17 | 177.7 (4) | C3—C8—C7—C6 | 0.1 (6) |
O6—N2—C22—C21 | −150.6 (4) | C3—C4—C5—C6 | 0.1 (6) |
O6—N2—C22—C17 | 27.7 (6) | C17—C16—C15—Br2 | −62.8 (4) |
O5—N2—C22—C21 | 26.3 (5) | C17—C16—C15—C1 | 175.8 (3) |
O5—N2—C22—C17 | −155.4 (4) | C22—C17—C18—C19 | −1.5 (6) |
N1—S1—C9—C10 | 65.9 (4) | C18—C17—C22—N2 | −174.7 (4) |
N1—S1—C9—C14 | −113.6 (3) | C18—C17—C22—C21 | 3.5 (6) |
N1—C4—C3—C2 | −1.4 (4) | C23—O4—C20—C19 | 5.7 (5) |
N1—C4—C3—C8 | −179.5 (4) | C23—O4—C20—C21 | −177.4 (4) |
N1—C4—C5—C6 | 178.0 (4) | C23—O3—C19—C20 | −7.1 (4) |
C20—O4—C23—O3 | −10.0 (4) | C23—O3—C19—C18 | 173.3 (4) |
C20—C19—C18—C17 | −1.8 (6) | C1—N1—C4—C3 | 2.9 (4) |
C20—C21—C22—N2 | 176.4 (4) | C1—N1—C4—C5 | −175.1 (4) |
C20—C21—C22—C17 | −1.9 (6) | C1—C2—C24—Br3 | −109.2 (4) |
C19—O3—C23—O4 | 10.5 (4) | C1—C2—C3—C8 | 177.1 (4) |
C19—C20—C21—C22 | −1.5 (6) | C1—C2—C3—C4 | −0.8 (5) |
C9—S1—N1—C4 | −104.3 (3) | C5—C4—C3—C2 | 176.9 (4) |
C9—S1—N1—C1 | 85.7 (4) | C5—C4—C3—C8 | −1.3 (6) |
C9—C10—C11—C12 | −0.5 (7) | C11—C12—C13—C14 | 0.9 (8) |
C9—C14—C13—C12 | −0.6 (7) | C14—C9—C10—C11 | 0.8 (6) |
C8—C7—C6—C5 | −1.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O5i | 0.95 | 2.58 | 3.525 (6) | 170 |
C13—H13···Cl13ii | 0.95 | 2.63 | 3.244 (8) | 123 |
C14—H14···O2iii | 0.95 | 2.57 | 3.518 (6) | 172 |
C1A—H1A···O1iv | 1.00 | 2.34 | 3.169 (15) | 140 |
C5—H5···O1 | 0.95 | 2.32 | 2.865 (6) | 116 |
C15—H15···O2 | 1.00 | 2.30 | 2.950 (5) | 122 |
C16—H16···O6 | 1.00 | 2.16 | 2.832 (5) | 123 |
C24—H24B···Br2 | 0.99 | 2.83 | 3.572 (4) | 132 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y, −z. |
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