organic compounds
(2Z)-2-Benzylidene-4-octadecyl-3,4-dihydro-2H-1,4-benzothiazin-3-one
aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de, Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: ellouz.chimie@gmail.com
The octadecyl chain in the title compound, C33H47NOS, is in the `fully extended' conformation. A puckering analysis of the thiazine ring was performed. The molecules form micellar blocks in the crystal by intercalation of the extended octadecyl chains and association of the dihydro benzothiazine units through C—H⋯O hydrogen bonds. These blocks are associated through intercalation of the pendant phenyl groups which reside on the outer edges of each block.
Keywords: crystal structure; dihydrobenzothiazine; hydrogen bond; micelle.
CCDC reference: 1548928
Structure description
1,4-Benzothiazine derivatives constitute an important class of et al., 2016a; Gupta et al., 2009). Several sulfur- and nitrogen-containing heterocycles have been well studied and various 1,4-benzothiazine derivatives have been synthesized by several methods (Dixit et al., 2008, 2009). Benzothiazines have found widespread application as antibacterial (Armenise et al., 2012; Sabatini et al., 2008), analgesic (Warren et al., 1987), anticancer (Jacquot et al., 2001) and anticonvulsant (Kalluraya et al., 2005) agents. As a continuation of our research work devoted to the development of N-substituted benzothiazine derivatives and evaluating their potential pharmacological activities, we have studied the condensation reaction of 1-bromooctadecane with (E)-2-(benzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one under conditions using tetra-n-butylammonium bromide (TBAB) as catalyst and potassium carbonate as base (Sebbar et al., 2016b, Sebbar et al., 2014; Ellouz et al., 2016). The of the compound obtained is reported in this work (Fig. 1).
which, even when part of a complex molecule, possess a wide spectrum of biological activities (SebbarIn the title compound, the octadecyl chain is in the `fully extended' conformation. A Cremer–Pople puckering analysis of the six-membered heterocyclic ring gave the parameters Q = 0.443 (1) Å, θ = 109.7 (2)° and φ = 154.3 (2)°. The pendant phenyl ring is rotationally disordered over two sites having approximately equal occupancy about the C9—C10 bond by 41.1 (2)°. The dihedral angle between the C10–C15 and the C1–C6 rings is 58.4 (1)° while that for the other component (C10A–C15A) is 32.9 (1)°. Intramolecular C—H⋯O and C—H⋯S interactions occur (Table 1 and Fig. 1).
In the crystal, the molecules form micellar blocks through intercalation of the octadecyl chains and association of the polar head groups along the c-axis direction through C3—H3⋯O1 hydrogen bonds (Table 2 and Fig. 2). These blocks are associated through intercalation of the pendant phenyl rings, which reside on the outer edges of each block (Fig. 2).
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Synthesis and crystallization
To a solution of 2-(benzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one (0.5 g, 2 mmol), potassium carbonate (0.55 g, 4 mmol) and tetra-n-butyl ammonium bromide (0.064 g, 0.2 mmol) in DMF (15 ml) was added 1-bromooctadecane (1.33 g, 4 mmol). Stirring was continued at room temperature for 12 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate–hexane (9/1) as The solid product was purified by recrystallization from ethanol solution to afford colourless crystals in 63% yield.
Refinement
Crystal data, data collection and structure . The pendant phenyl ring is rotationally disordered over two sites having approximately equal occupancy [ratio 0.503 (4):0.497 (4)]. The two components were refined as rigid hexagons with the attached hydrogen atoms in idealized positions.
details are summarized in Table 2Structural data
CCDC reference: 1548928
https://doi.org/10.1107/S2414314617006952/zq4019sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006952/zq4019Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006952/zq4019Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006952/zq4019Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C33H47NOS | F(000) = 1104 |
Mr = 505.77 | Dx = 1.164 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 33.8411 (7) Å | Cell parameters from 9991 reflections |
b = 4.7106 (1) Å | θ = 2.6–74.7° |
c = 18.0987 (4) Å | µ = 1.17 mm−1 |
β = 90.470 (1)° | T = 150 K |
V = 2885.05 (11) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.11 × 0.03 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 5792 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 4927 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.040 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 74.7°, θmin = 2.6° |
ω scans | h = −42→42 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −5→5 |
Tmin = 0.81, Tmax = 0.97 | l = −21→22 |
21375 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: mixed |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0511P)2 + 1.3651P] where P = (Fo2 + 2Fc2)/3 |
5792 reflections | (Δ/σ)max < 0.001 |
524 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.46 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The pendant phenyl ring is rotationally disordered over two sites having approximately equal occupancies. The two components were refined as rigid hexagons with the attached hydrogen atoms in idealized positions. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.10593 (2) | 0.77362 (9) | 0.55251 (2) | 0.03197 (13) | |
O1 | 0.17114 (4) | 0.2595 (3) | 0.43940 (7) | 0.0463 (4) | |
N1 | 0.17320 (4) | 0.3357 (3) | 0.56293 (7) | 0.0261 (3) | |
C1 | 0.15506 (4) | 0.4140 (3) | 0.63057 (8) | 0.0245 (3) | |
C2 | 0.16804 (5) | 0.2944 (4) | 0.69743 (9) | 0.0295 (3) | |
H2 | 0.1873 (6) | 0.151 (4) | 0.6974 (10) | 0.033 (5)* | |
C3 | 0.15261 (5) | 0.3838 (4) | 0.76417 (9) | 0.0348 (4) | |
H3 | 0.1623 (6) | 0.303 (5) | 0.8089 (12) | 0.047 (6)* | |
C4 | 0.12362 (5) | 0.5891 (4) | 0.76594 (10) | 0.0358 (4) | |
H4 | 0.1125 (7) | 0.651 (5) | 0.8107 (13) | 0.051 (6)* | |
C5 | 0.10945 (5) | 0.7024 (4) | 0.70018 (10) | 0.0339 (4) | |
H5 | 0.0881 (6) | 0.846 (5) | 0.7002 (11) | 0.040 (5)* | |
C6 | 0.12506 (4) | 0.6157 (3) | 0.63291 (9) | 0.0270 (3) | |
C7 | 0.11658 (4) | 0.5095 (4) | 0.48802 (9) | 0.0273 (3) | |
C8 | 0.15556 (5) | 0.3606 (4) | 0.49388 (9) | 0.0302 (4) | |
C9 | 0.09375 (5) | 0.4468 (4) | 0.42866 (9) | 0.0291 (3) | |
H9 | 0.1057 (6) | 0.313 (4) | 0.3946 (10) | 0.032 (5)* | |
C10 | 0.05477 (6) | 0.5456 (5) | 0.40246 (18) | 0.031 (2) | 0.503 (4) |
C11 | 0.03828 (7) | 0.7998 (5) | 0.42615 (15) | 0.0306 (9) | 0.503 (4) |
H11 | 0.0532 | 0.9248 | 0.4566 | 0.037* | 0.503 (4) |
C12 | −0.00007 (7) | 0.8709 (5) | 0.40525 (15) | 0.0349 (9) | 0.503 (4) |
H12 | −0.0113 | 1.0446 | 0.4214 | 0.042* | 0.503 (4) |
C13 | −0.02194 (6) | 0.6879 (6) | 0.36066 (17) | 0.036 (2) | 0.503 (4) |
H13 | −0.0482 | 0.7366 | 0.3464 | 0.043* | 0.503 (4) |
C14 | −0.00545 (9) | 0.4338 (6) | 0.3370 (2) | 0.0456 (12) | 0.503 (4) |
H14 | −0.0204 | 0.3088 | 0.3065 | 0.055* | 0.503 (4) |
C15 | 0.03290 (9) | 0.3627 (5) | 0.3579 (2) | 0.0388 (10) | 0.503 (4) |
H15 | 0.0442 | 0.1890 | 0.3417 | 0.047* | 0.503 (4) |
C10A | 0.05253 (6) | 0.5378 (6) | 0.41016 (14) | 0.0224 (19) | 0.497 (4) |
C11A | 0.02588 (7) | 0.6580 (6) | 0.45914 (11) | 0.0300 (9) | 0.497 (4) |
H11A | 0.0339 | 0.6986 | 0.5085 | 0.036* | 0.497 (4) |
C12A | −0.01246 (6) | 0.7186 (6) | 0.43597 (13) | 0.0313 (9) | 0.497 (4) |
H12A | −0.0307 | 0.8006 | 0.4694 | 0.038* | 0.497 (4) |
C13A | −0.02416 (6) | 0.6590 (7) | 0.36382 (13) | 0.034 (2) | 0.497 (4) |
H13A | −0.0504 | 0.7004 | 0.3480 | 0.040* | 0.497 (4) |
C14A | 0.00249 (8) | 0.5389 (7) | 0.31484 (10) | 0.0345 (10) | 0.497 (4) |
H14A | −0.0055 | 0.4982 | 0.2655 | 0.041* | 0.497 (4) |
C15A | 0.04083 (7) | 0.4783 (7) | 0.33801 (13) | 0.0297 (9) | 0.497 (4) |
H15A | 0.0590 | 0.3962 | 0.3045 | 0.036* | 0.497 (4) |
C16 | 0.21002 (5) | 0.1695 (4) | 0.56682 (10) | 0.0298 (4) | |
H16A | 0.2051 (6) | −0.004 (5) | 0.5980 (11) | 0.037 (5)* | |
H16B | 0.2162 (6) | 0.114 (5) | 0.5165 (12) | 0.043 (6)* | |
C17 | 0.24455 (5) | 0.3396 (4) | 0.59860 (10) | 0.0304 (4) | |
H17A | 0.2350 (6) | 0.459 (5) | 0.6395 (11) | 0.039 (5)* | |
H17B | 0.2534 (6) | 0.473 (5) | 0.5603 (12) | 0.043 (6)* | |
C18 | 0.27795 (5) | 0.1485 (4) | 0.62544 (11) | 0.0333 (4) | |
H18A | 0.2663 (6) | 0.011 (5) | 0.6624 (12) | 0.045 (6)* | |
H18B | 0.2885 (6) | 0.046 (5) | 0.5832 (12) | 0.047 (6)* | |
C19 | 0.31103 (5) | 0.3118 (4) | 0.66399 (10) | 0.0331 (4) | |
H19A | 0.2991 (6) | 0.421 (4) | 0.7056 (11) | 0.038 (5)* | |
H19B | 0.3222 (6) | 0.448 (5) | 0.6307 (11) | 0.040 (5)* | |
C20 | 0.34370 (5) | 0.1221 (4) | 0.69465 (11) | 0.0363 (4) | |
H20A | 0.3316 (6) | −0.017 (5) | 0.7293 (12) | 0.046 (6)* | |
H20B | 0.3545 (7) | 0.012 (5) | 0.6542 (13) | 0.052 (6)* | |
C21 | 0.37560 (5) | 0.2852 (4) | 0.73656 (11) | 0.0365 (4) | |
H21A | 0.3627 (6) | 0.390 (5) | 0.7799 (12) | 0.045 (6)* | |
H21B | 0.3879 (6) | 0.424 (5) | 0.7029 (12) | 0.045 (6)* | |
C22 | 0.40833 (5) | 0.0963 (5) | 0.76801 (11) | 0.0379 (4) | |
H22A | 0.3964 (7) | −0.048 (5) | 0.8017 (13) | 0.051 (6)* | |
H22B | 0.4214 (7) | −0.016 (5) | 0.7276 (13) | 0.052 (6)* | |
C23 | 0.43998 (5) | 0.2610 (5) | 0.81015 (11) | 0.0386 (4) | |
H23A | 0.4269 (6) | 0.369 (5) | 0.8512 (12) | 0.046 (6)* | |
H23B | 0.4523 (7) | 0.398 (5) | 0.7763 (12) | 0.048 (6)* | |
C24 | 0.47278 (5) | 0.0739 (5) | 0.84179 (11) | 0.0391 (4) | |
H24A | 0.4852 (7) | −0.046 (5) | 0.8010 (13) | 0.057 (7)* | |
H24B | 0.4609 (7) | −0.072 (5) | 0.8751 (13) | 0.053 (6)* | |
C25 | 0.50452 (5) | 0.2404 (5) | 0.88337 (11) | 0.0389 (4) | |
H25A | 0.4916 (6) | 0.354 (5) | 0.9245 (12) | 0.047 (6)* | |
H25B | 0.5166 (7) | 0.384 (5) | 0.8489 (12) | 0.050 (6)* | |
C26 | 0.53738 (5) | 0.0544 (5) | 0.91556 (11) | 0.0386 (4) | |
H26A | 0.5498 (7) | −0.069 (5) | 0.8743 (13) | 0.052 (6)* | |
H26B | 0.5253 (6) | −0.087 (5) | 0.9512 (12) | 0.046 (6)* | |
C27 | 0.56926 (5) | 0.2235 (5) | 0.95610 (11) | 0.0388 (4) | |
H27A | 0.5568 (7) | 0.338 (5) | 0.9957 (12) | 0.049 (6)* | |
H27B | 0.5805 (6) | 0.363 (5) | 0.9208 (12) | 0.046 (6)* | |
C28 | 0.60229 (5) | 0.0411 (4) | 0.98870 (11) | 0.0374 (4) | |
H28A | 0.5905 (6) | −0.100 (5) | 1.0231 (11) | 0.039 (5)* | |
H28B | 0.6146 (6) | −0.083 (5) | 0.9474 (12) | 0.044 (6)* | |
C29 | 0.63446 (5) | 0.2137 (4) | 1.02729 (11) | 0.0374 (4) | |
H29A | 0.6453 (7) | 0.356 (5) | 0.9902 (13) | 0.053 (6)* | |
H29B | 0.6224 (6) | 0.331 (5) | 1.0664 (12) | 0.045 (6)* | |
C30 | 0.66771 (5) | 0.0345 (4) | 1.06014 (10) | 0.0355 (4) | |
H30A | 0.6799 (6) | −0.094 (5) | 1.0206 (12) | 0.047 (6)* | |
H30B | 0.6561 (6) | −0.098 (5) | 1.0982 (11) | 0.042 (6)* | |
C31 | 0.70000 (5) | 0.2102 (4) | 1.09748 (11) | 0.0374 (4) | |
H31A | 0.6871 (7) | 0.327 (5) | 1.1351 (13) | 0.052 (6)* | |
H31B | 0.7112 (7) | 0.341 (5) | 1.0589 (13) | 0.057 (7)* | |
C32 | 0.73361 (5) | 0.0345 (4) | 1.13048 (11) | 0.0392 (4) | |
H32A | 0.7216 (7) | −0.103 (5) | 1.1672 (13) | 0.053 (6)* | |
H32B | 0.7455 (7) | −0.088 (5) | 1.0913 (13) | 0.054 (6)* | |
C33 | 0.76560 (6) | 0.2158 (5) | 1.16623 (14) | 0.0476 (5) | |
H33A | 0.7546 (8) | 0.322 (6) | 1.2070 (15) | 0.067 (8)* | |
H33B | 0.7871 (8) | 0.105 (6) | 1.1857 (14) | 0.065 (7)* | |
H33C | 0.7764 (8) | 0.352 (6) | 1.1291 (16) | 0.076 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0329 (2) | 0.0295 (2) | 0.0333 (2) | 0.00240 (16) | −0.01019 (16) | 0.00035 (16) |
O1 | 0.0316 (6) | 0.0827 (11) | 0.0247 (6) | 0.0151 (7) | −0.0012 (5) | −0.0048 (6) |
N1 | 0.0202 (6) | 0.0350 (7) | 0.0230 (6) | −0.0002 (5) | −0.0045 (5) | −0.0004 (5) |
C1 | 0.0185 (6) | 0.0308 (8) | 0.0240 (7) | −0.0039 (6) | −0.0033 (6) | −0.0003 (6) |
C2 | 0.0244 (7) | 0.0367 (9) | 0.0272 (8) | 0.0018 (7) | −0.0040 (6) | 0.0034 (7) |
C3 | 0.0333 (8) | 0.0463 (10) | 0.0248 (8) | −0.0042 (8) | −0.0043 (7) | 0.0030 (7) |
C4 | 0.0350 (9) | 0.0454 (10) | 0.0270 (8) | −0.0031 (8) | 0.0017 (7) | −0.0054 (7) |
C5 | 0.0293 (8) | 0.0375 (9) | 0.0349 (9) | 0.0003 (7) | −0.0012 (7) | −0.0046 (7) |
C6 | 0.0226 (7) | 0.0293 (8) | 0.0290 (8) | −0.0039 (6) | −0.0047 (6) | −0.0008 (6) |
C7 | 0.0232 (7) | 0.0326 (8) | 0.0260 (8) | −0.0018 (6) | −0.0018 (6) | 0.0052 (6) |
C8 | 0.0230 (7) | 0.0426 (9) | 0.0250 (8) | −0.0015 (7) | −0.0035 (6) | 0.0017 (7) |
C9 | 0.0249 (7) | 0.0373 (9) | 0.0251 (8) | −0.0019 (7) | −0.0027 (6) | 0.0035 (7) |
C10 | 0.016 (3) | 0.035 (5) | 0.043 (4) | −0.004 (3) | 0.007 (3) | 0.003 (3) |
C11 | 0.0276 (16) | 0.036 (2) | 0.0277 (17) | −0.0018 (14) | −0.0063 (14) | 0.0041 (15) |
C12 | 0.0316 (17) | 0.041 (2) | 0.0325 (18) | 0.0055 (16) | −0.0018 (14) | 0.0077 (16) |
C13 | 0.024 (3) | 0.037 (3) | 0.047 (5) | 0.004 (3) | −0.012 (3) | 0.016 (3) |
C14 | 0.033 (2) | 0.052 (3) | 0.052 (3) | −0.008 (2) | −0.021 (2) | 0.005 (2) |
C15 | 0.033 (2) | 0.040 (2) | 0.043 (2) | −0.0020 (18) | −0.0105 (17) | −0.0011 (19) |
C10A | 0.030 (3) | 0.028 (4) | 0.009 (2) | −0.004 (3) | −0.012 (2) | 0.009 (2) |
C11A | 0.0283 (16) | 0.0331 (19) | 0.0285 (18) | −0.0023 (14) | −0.0025 (14) | 0.0014 (15) |
C12A | 0.0259 (16) | 0.0324 (19) | 0.0357 (19) | −0.0026 (14) | −0.0003 (14) | 0.0028 (15) |
C13A | 0.028 (4) | 0.039 (4) | 0.035 (4) | −0.009 (3) | −0.006 (3) | 0.007 (3) |
C14A | 0.034 (2) | 0.041 (2) | 0.029 (2) | −0.0054 (17) | −0.0120 (16) | 0.0041 (16) |
C15A | 0.0301 (18) | 0.036 (2) | 0.0224 (19) | 0.0003 (16) | −0.0055 (14) | 0.0004 (15) |
C16 | 0.0222 (7) | 0.0362 (9) | 0.0308 (9) | 0.0022 (7) | −0.0042 (6) | −0.0034 (7) |
C17 | 0.0195 (7) | 0.0363 (9) | 0.0352 (9) | 0.0005 (7) | −0.0031 (6) | 0.0007 (7) |
C18 | 0.0218 (7) | 0.0388 (9) | 0.0393 (10) | 0.0013 (7) | −0.0058 (7) | −0.0014 (8) |
C19 | 0.0209 (7) | 0.0401 (10) | 0.0383 (9) | 0.0013 (7) | −0.0051 (7) | −0.0007 (8) |
C20 | 0.0219 (7) | 0.0456 (11) | 0.0413 (10) | 0.0032 (7) | −0.0058 (7) | −0.0013 (9) |
C21 | 0.0223 (8) | 0.0477 (11) | 0.0395 (10) | 0.0005 (7) | −0.0054 (7) | −0.0001 (8) |
C22 | 0.0223 (8) | 0.0505 (11) | 0.0408 (10) | 0.0019 (8) | −0.0048 (7) | −0.0015 (9) |
C23 | 0.0235 (8) | 0.0538 (12) | 0.0385 (10) | 0.0007 (8) | −0.0063 (7) | 0.0008 (9) |
C24 | 0.0223 (8) | 0.0557 (12) | 0.0392 (10) | 0.0023 (8) | −0.0053 (7) | −0.0025 (9) |
C25 | 0.0238 (8) | 0.0555 (12) | 0.0373 (10) | −0.0001 (8) | −0.0067 (7) | 0.0012 (9) |
C26 | 0.0233 (8) | 0.0538 (12) | 0.0385 (10) | 0.0024 (8) | −0.0048 (7) | −0.0028 (9) |
C27 | 0.0261 (8) | 0.0523 (12) | 0.0378 (10) | 0.0012 (8) | −0.0067 (7) | 0.0016 (9) |
C28 | 0.0245 (8) | 0.0507 (11) | 0.0369 (10) | 0.0025 (8) | −0.0057 (7) | −0.0034 (8) |
C29 | 0.0274 (8) | 0.0457 (11) | 0.0388 (10) | 0.0019 (8) | −0.0086 (7) | 0.0006 (8) |
C30 | 0.0261 (8) | 0.0436 (10) | 0.0367 (9) | 0.0040 (7) | −0.0061 (7) | −0.0018 (8) |
C31 | 0.0306 (8) | 0.0414 (10) | 0.0402 (10) | 0.0044 (8) | −0.0111 (8) | 0.0006 (8) |
C32 | 0.0309 (8) | 0.0441 (11) | 0.0424 (10) | 0.0060 (8) | −0.0091 (8) | −0.0007 (9) |
C33 | 0.0365 (10) | 0.0537 (13) | 0.0524 (13) | 0.0048 (9) | −0.0201 (9) | −0.0014 (10) |
S1—C7 | 1.7456 (17) | C18—C19 | 1.523 (2) |
S1—C6 | 1.7536 (16) | C18—H18A | 1.01 (2) |
O1—C8 | 1.219 (2) | C18—H18B | 0.98 (2) |
N1—C8 | 1.386 (2) | C19—C20 | 1.523 (2) |
N1—C1 | 1.423 (2) | C19—H19A | 1.00 (2) |
N1—C16 | 1.473 (2) | C19—H19B | 0.96 (2) |
C1—C6 | 1.391 (2) | C20—C21 | 1.522 (2) |
C1—C2 | 1.402 (2) | C20—H20A | 1.00 (2) |
C2—C3 | 1.385 (2) | C20—H20B | 0.97 (2) |
C2—H2 | 0.94 (2) | C21—C22 | 1.527 (2) |
C3—C4 | 1.378 (3) | C21—H21A | 1.03 (2) |
C3—H3 | 0.95 (2) | C21—H21B | 0.99 (2) |
C4—C5 | 1.386 (3) | C22—C23 | 1.522 (3) |
C4—H4 | 0.94 (2) | C22—H22A | 1.00 (2) |
C5—C6 | 1.392 (2) | C22—H22B | 1.01 (2) |
C5—H5 | 0.99 (2) | C23—C24 | 1.525 (3) |
C7—C9 | 1.351 (2) | C23—H23A | 1.01 (2) |
C7—C8 | 1.497 (2) | C23—H23B | 0.99 (2) |
C9—C10 | 1.474 (2) | C24—C25 | 1.524 (3) |
C9—C10A | 1.495 (2) | C24—H24A | 1.02 (2) |
C9—H9 | 0.97 (2) | C24—H24B | 1.00 (2) |
C10—C11 | 1.3900 | C25—C26 | 1.527 (3) |
C10—C15 | 1.3900 | C25—H25A | 1.02 (2) |
C11—C12 | 1.3900 | C25—H25B | 1.01 (2) |
C11—H11 | 0.9500 | C26—C27 | 1.524 (3) |
C12—C13 | 1.3900 | C26—H26A | 1.04 (2) |
C12—H12 | 0.9500 | C26—H26B | 1.02 (2) |
C13—C14 | 1.3900 | C27—C28 | 1.525 (2) |
C13—H13 | 0.9500 | C27—H27A | 0.99 (2) |
C14—C15 | 1.3900 | C27—H27B | 0.99 (2) |
C14—H14 | 0.9500 | C28—C29 | 1.524 (3) |
C15—H15 | 0.9500 | C28—H28A | 1.00 (2) |
C10A—C11A | 1.3900 | C28—H28B | 1.04 (2) |
C10A—C15A | 1.3900 | C29—C30 | 1.524 (2) |
C11A—C12A | 1.3900 | C29—H29A | 1.02 (2) |
C11A—H11A | 0.9500 | C29—H29B | 0.99 (2) |
C12A—C13A | 1.3900 | C30—C31 | 1.524 (2) |
C12A—H12A | 0.9500 | C30—H30A | 1.03 (2) |
C13A—C14A | 1.3900 | C30—H30B | 1.01 (2) |
C13A—H13A | 0.9500 | C31—C32 | 1.525 (2) |
C14A—C15A | 1.3900 | C31—H31A | 0.98 (2) |
C14A—H14A | 0.9500 | C31—H31B | 1.01 (3) |
C15A—H15A | 0.9500 | C32—C33 | 1.519 (3) |
C16—C17 | 1.526 (2) | C32—H32A | 1.02 (2) |
C16—H16A | 1.01 (2) | C32—H32B | 1.00 (2) |
C16—H16B | 0.97 (2) | C33—H33A | 0.97 (3) |
C17—C18 | 1.521 (2) | C33—H33B | 0.96 (3) |
C17—H17A | 0.99 (2) | C33—H33C | 1.00 (3) |
C17—H17B | 0.98 (2) | ||
C7—S1—C6 | 100.11 (8) | C18—C19—H19A | 107.8 (12) |
C8—N1—C1 | 124.64 (13) | C20—C19—H19B | 109.4 (12) |
C8—N1—C16 | 116.50 (13) | C18—C19—H19B | 110.0 (12) |
C1—N1—C16 | 117.88 (13) | H19A—C19—H19B | 107.0 (17) |
C6—C1—C2 | 118.13 (15) | C21—C20—C19 | 113.28 (16) |
C6—C1—N1 | 121.57 (14) | C21—C20—H20A | 108.1 (12) |
C2—C1—N1 | 120.28 (14) | C19—C20—H20A | 108.3 (12) |
C3—C2—C1 | 120.85 (16) | C21—C20—H20B | 112.1 (13) |
C3—C2—H2 | 119.1 (11) | C19—C20—H20B | 108.3 (13) |
C1—C2—H2 | 120.0 (11) | H20A—C20—H20B | 106.3 (18) |
C4—C3—C2 | 120.47 (16) | C20—C21—C22 | 113.64 (16) |
C4—C3—H3 | 120.2 (13) | C20—C21—H21A | 108.6 (12) |
C2—C3—H3 | 119.3 (13) | C22—C21—H21A | 107.9 (12) |
C3—C4—C5 | 119.42 (17) | C20—C21—H21B | 109.1 (12) |
C3—C4—H4 | 121.7 (14) | C22—C21—H21B | 107.9 (13) |
C5—C4—H4 | 118.8 (14) | H21A—C21—H21B | 109.7 (18) |
C4—C5—C6 | 120.45 (17) | C23—C22—C21 | 113.26 (17) |
C4—C5—H5 | 120.6 (12) | C23—C22—H22A | 109.1 (13) |
C6—C5—H5 | 118.9 (12) | C21—C22—H22A | 109.2 (13) |
C1—C6—C5 | 120.61 (15) | C23—C22—H22B | 108.7 (13) |
C1—C6—S1 | 121.94 (12) | C21—C22—H22B | 110.8 (13) |
C5—C6—S1 | 117.44 (13) | H22A—C22—H22B | 105.5 (19) |
C9—C7—C8 | 116.86 (15) | C22—C23—C24 | 113.61 (17) |
C9—C7—S1 | 124.60 (13) | C22—C23—H23A | 108.4 (12) |
C8—C7—S1 | 118.24 (11) | C24—C23—H23A | 109.8 (12) |
O1—C8—N1 | 120.71 (15) | C22—C23—H23B | 108.8 (13) |
O1—C8—C7 | 120.83 (14) | C24—C23—H23B | 107.6 (13) |
N1—C8—C7 | 118.45 (14) | H23A—C23—H23B | 108.4 (19) |
C7—C9—C10 | 133.75 (18) | C25—C24—C23 | 113.32 (17) |
C7—C9—C10A | 129.94 (18) | C25—C24—H24A | 110.4 (14) |
C7—C9—H9 | 114.1 (11) | C23—C24—H24A | 110.5 (13) |
C10—C9—H9 | 112.1 (11) | C25—C24—H24B | 109.9 (13) |
C10A—C9—H9 | 115.8 (11) | C23—C24—H24B | 109.2 (13) |
C11—C10—C15 | 120.0 | H24A—C24—H24B | 103.0 (19) |
C11—C10—C9 | 122.23 (17) | C24—C25—C26 | 113.65 (17) |
C15—C10—C9 | 117.51 (17) | C24—C25—H25A | 109.0 (12) |
C12—C11—C10 | 120.0 | C26—C25—H25A | 109.8 (12) |
C12—C11—H11 | 120.0 | C24—C25—H25B | 109.1 (13) |
C10—C11—H11 | 120.0 | C26—C25—H25B | 109.0 (13) |
C13—C12—C11 | 120.0 | H25A—C25—H25B | 106.0 (18) |
C13—C12—H12 | 120.0 | C27—C26—C25 | 113.19 (17) |
C11—C12—H12 | 120.0 | C27—C26—H26A | 110.5 (13) |
C12—C13—C14 | 120.0 | C25—C26—H26A | 110.1 (13) |
C12—C13—H13 | 120.0 | C27—C26—H26B | 108.9 (12) |
C14—C13—H13 | 120.0 | C25—C26—H26B | 108.9 (12) |
C13—C14—C15 | 120.0 | H26A—C26—H26B | 104.9 (18) |
C13—C14—H14 | 120.0 | C26—C27—C28 | 113.91 (17) |
C15—C14—H14 | 120.0 | C26—C27—H27A | 109.1 (13) |
C14—C15—C10 | 120.0 | C28—C27—H27A | 109.9 (13) |
C14—C15—H15 | 120.0 | C26—C27—H27B | 108.0 (13) |
C10—C15—H15 | 120.0 | C28—C27—H27B | 109.8 (13) |
C11A—C10A—C15A | 120.0 | H27A—C27—H27B | 105.9 (19) |
C11A—C10A—C9 | 125.66 (17) | C29—C28—C27 | 113.29 (17) |
C15A—C10A—C9 | 114.25 (17) | C29—C28—H28A | 111.0 (12) |
C10A—C11A—C12A | 120.0 | C27—C28—H28A | 108.8 (12) |
C10A—C11A—H11A | 120.0 | C29—C28—H28B | 109.9 (12) |
C12A—C11A—H11A | 120.0 | C27—C28—H28B | 109.6 (12) |
C13A—C12A—C11A | 120.0 | H28A—C28—H28B | 103.8 (17) |
C13A—C12A—H12A | 120.0 | C30—C29—C28 | 113.95 (16) |
C11A—C12A—H12A | 120.0 | C30—C29—H29A | 110.6 (13) |
C12A—C13A—C14A | 120.0 | C28—C29—H29A | 108.0 (13) |
C12A—C13A—H13A | 120.0 | C30—C29—H29B | 109.7 (13) |
C14A—C13A—H13A | 120.0 | C28—C29—H29B | 109.2 (13) |
C15A—C14A—C13A | 120.0 | H29A—C29—H29B | 105.0 (18) |
C15A—C14A—H14A | 120.0 | C29—C30—C31 | 113.38 (16) |
C13A—C14A—H14A | 120.0 | C29—C30—H30A | 110.7 (12) |
C14A—C15A—C10A | 120.0 | C31—C30—H30A | 109.8 (12) |
C14A—C15A—H15A | 120.0 | C29—C30—H30B | 108.5 (12) |
C10A—C15A—H15A | 120.0 | C31—C30—H30B | 108.3 (12) |
N1—C16—C17 | 112.56 (14) | H30A—C30—H30B | 105.8 (18) |
N1—C16—H16A | 108.3 (11) | C30—C31—C32 | 114.12 (16) |
C17—C16—H16A | 110.1 (11) | C30—C31—H31A | 106.9 (14) |
N1—C16—H16B | 106.6 (12) | C32—C31—H31A | 111.5 (13) |
C17—C16—H16B | 108.8 (13) | C30—C31—H31B | 107.2 (14) |
H16A—C16—H16B | 110.3 (17) | C32—C31—H31B | 108.7 (14) |
C18—C17—C16 | 111.98 (15) | H31A—C31—H31B | 108 (2) |
C18—C17—H17A | 110.1 (12) | C33—C32—C31 | 112.85 (17) |
C16—C17—H17A | 109.3 (12) | C33—C32—H32A | 111.6 (13) |
C18—C17—H17B | 111.8 (12) | C31—C32—H32A | 107.6 (13) |
C16—C17—H17B | 107.8 (12) | C33—C32—H32B | 109.6 (13) |
H17A—C17—H17B | 105.5 (17) | C31—C32—H32B | 109.8 (13) |
C17—C18—C19 | 112.89 (15) | H32A—C32—H32B | 105.1 (19) |
C17—C18—H18A | 107.3 (12) | C32—C33—H33A | 109.8 (16) |
C19—C18—H18A | 107.9 (12) | C32—C33—H33B | 112.7 (16) |
C17—C18—H18B | 108.6 (13) | H33A—C33—H33B | 107 (2) |
C19—C18—H18B | 109.7 (13) | C32—C33—H33C | 109.8 (16) |
H18A—C18—H18B | 110.3 (18) | H33A—C33—H33C | 109 (2) |
C20—C19—C18 | 113.54 (16) | H33B—C33—H33C | 108 (2) |
C20—C19—H19A | 108.8 (12) | ||
C8—N1—C1—C6 | −24.7 (2) | C10—C11—C12—C13 | 0.0 |
C16—N1—C1—C6 | 167.07 (14) | C11—C12—C13—C14 | 0.0 |
C8—N1—C1—C2 | 157.30 (16) | C12—C13—C14—C15 | 0.0 |
C16—N1—C1—C2 | −10.9 (2) | C13—C14—C15—C10 | 0.0 |
C6—C1—C2—C3 | −2.8 (2) | C11—C10—C15—C14 | 0.0 |
N1—C1—C2—C3 | 175.29 (15) | C9—C10—C15—C14 | 174.3 (3) |
C1—C2—C3—C4 | 1.2 (3) | C7—C9—C10A—C11A | −15.3 (3) |
C2—C3—C4—C5 | 1.1 (3) | C7—C9—C10A—C15A | 168.19 (19) |
C3—C4—C5—C6 | −1.7 (3) | C15A—C10A—C11A—C12A | 0.0 |
C2—C1—C6—C5 | 2.2 (2) | C9—C10A—C11A—C12A | −176.3 (3) |
N1—C1—C6—C5 | −175.88 (15) | C10A—C11A—C12A—C13A | 0.0 |
C2—C1—C6—S1 | −178.72 (12) | C11A—C12A—C13A—C14A | 0.0 |
N1—C1—C6—S1 | 3.2 (2) | C12A—C13A—C14A—C15A | 0.0 |
C4—C5—C6—C1 | 0.1 (3) | C13A—C14A—C15A—C10A | 0.0 |
C4—C5—C6—S1 | −179.09 (14) | C11A—C10A—C15A—C14A | 0.0 |
C7—S1—C6—C1 | 25.40 (15) | C9—C10A—C15A—C14A | 176.7 (2) |
C7—S1—C6—C5 | −155.46 (13) | C8—N1—C16—C17 | 122.78 (16) |
C6—S1—C7—C9 | 146.07 (15) | C1—N1—C16—C17 | −68.02 (19) |
C6—S1—C7—C8 | −40.46 (14) | N1—C16—C17—C18 | 161.52 (15) |
C1—N1—C8—O1 | −171.61 (16) | C16—C17—C18—C19 | −174.54 (15) |
C16—N1—C8—O1 | −3.2 (2) | C17—C18—C19—C20 | 177.06 (16) |
C1—N1—C8—C7 | 7.2 (2) | C18—C19—C20—C21 | −177.02 (16) |
C16—N1—C8—C7 | 175.62 (14) | C19—C20—C21—C22 | 179.56 (16) |
C9—C7—C8—O1 | 21.7 (3) | C20—C21—C22—C23 | −179.70 (16) |
S1—C7—C8—O1 | −152.32 (15) | C21—C22—C23—C24 | 179.97 (16) |
C9—C7—C8—N1 | −157.19 (16) | C22—C23—C24—C25 | 179.53 (16) |
S1—C7—C8—N1 | 28.8 (2) | C23—C24—C25—C26 | 179.72 (16) |
C8—C7—C9—C10 | −179.2 (2) | C24—C25—C26—C27 | 179.20 (16) |
S1—C7—C9—C10 | −5.6 (3) | C25—C26—C27—C28 | 179.93 (16) |
C8—C7—C9—C10A | 174.2 (2) | C26—C27—C28—C29 | 178.50 (16) |
S1—C7—C9—C10A | −12.3 (3) | C27—C28—C29—C30 | −179.97 (16) |
C7—C9—C10—C11 | 20.0 (4) | C28—C29—C30—C31 | 179.07 (16) |
C7—C9—C10—C15 | −154.1 (2) | C29—C30—C31—C32 | −179.82 (17) |
C15—C10—C11—C12 | 0.0 | C30—C31—C32—C33 | 179.12 (18) |
C9—C10—C11—C12 | −174.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.95 (2) | 2.40 (2) | 3.298 (2) | 158.0 (18) |
C9—H9···O1 | 0.97 (2) | 2.367 (19) | 2.769 (2) | 104.1 (13) |
C11—H11···S1 | 0.95 | 2.58 | 3.225 (2) | 126 |
C16—H16B···O1 | 0.97 (2) | 2.17 (2) | 2.679 (2) | 111.3 (15) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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