organic compounds
3-(2,2-Dioxo-3,4-dihydrobenzo[e][1,2,3]oxathiazin-4-yl)-3-fluoro-1-phenylindolin-2-one
aCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, People's Republic of China
*Correspondence e-mail: lingyan.chen@hotmail.com
The title compound, C21H15FN2O4S, contains two chiral carbon centres, but crystal symmetry generates a The features N—H⋯O hydrogen bonding. The sulfonate group is disordered with an occupancy ratio of 0.933 (4):0.067 (4).
Keywords: crystal structure; fluorine; sulfamidate.
CCDC reference: 1971616
Structure description
The incorporation of one or more fluorine atoms into an organic molecule can result in improved thermal/metabolic stability, bioactivity and et al., 2008). In this context, the β-fluoroamine motif is an important structural feature and has been found in a number of drug candidates (Zhao et al., 2019). Consequently, the synthesis of chiral molecules with a fluorinated carbon center has attracted recent attention (Shang et al., 2015; Chen et al., 2017; Paladhi et al., 2017; Zheng et al., 2018). As part of our work in this area, we now describe the synthesis and structure of the title compound (Fig. 1).
(PurserThe geometric parameters do not show any unusual features. In the crystal, molecules are connected by pairwise N—H⋯O hydrogen bonds (Table 1, Fig. 2) to generate centrosymmetric R22(12) loops.
Synthesis and crystallization
Under an N2 atmosphere, a 10 mL reaction tube was charged with 3-fluoro-1-phenylindolin-2-one (0.24 mmol), catalyst 4-[(S)-(benzyloxy)(1S,2R,4S,5R)-5-vinylquinuclidin-2-yl]methyl)quinolin-6-ol (12.0 mg, 0.03 mmol) and dried CHCl3 (2.0 ml). The reaction mixture was cooled to 0°C, followed by the addition of benzo[e][1,2,3]oxathiazine 2,2-dioxide (0.2 mmol). The reaction mixture was stirred at 0°C until the complete conversion of benzo[e][1,2,3]oxathiazine 2,2-dioxide, and was then purified by flash to give the desired product (80.4 mg, 98%). Crystals were grown from petroleum ether/ethyl acetate solution. Data: [α]22D= −32.9 (c = 0.54, CHCl3); m.p. 210.2–211.3°C. 1H NMR (500 MHz, DMSO-d6) δ 9.37 (s, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.65 (d, J = 7.7 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.59 (d, J = 7.8 Hz, 1H), 7.53 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 6.7 Hz, 3H), 7.36 (t, J = 7.7 Hz, 1H), 7.24 (d, J = 8.2 Hz, 1H), 6.94 (t, J = 7.6 Hz, 1H), 6.76 (d, J = 7.9 Hz, 1H), 6.51 (d, J = 7.4 Hz, 1H), 5.52 (d, J = 12.6 Hz, 1H). 19F NMR (471 MHz, DMSO-d6) δ −150.20 (s). 13C NMR (126 MHz, DMSO-d6) δ 169.95 (d, J = 20.0 Hz), 151.80 (s), 145.74 (d, J = 6.2 Hz), 133.63 (s), 132.67 (d, J = 3.2 Hz), 131.46 (s), 130.38 (s), 129.20 (s), 129.00 (d, J = 7.7 Hz), 126.93 (s), 126.21 (d, J = 4.5 Hz), 123.76 (d, J = 2.9 Hz), 122.17 (s), 122.03 (s), 119.37 (s), 118.12 (d, J = 1.7 Hz), 110.44 (s), 93.67 (d, J = 190.8 Hz), 58.82 (d, J = 35.1 Hz).
Refinement
Crystal data, data collection and structure . The disordered sulfonate group was treated using a PART command in the The occupancy factors were restrained to sum to unity. The refined occupancy ratio is 0.933 (4):0.067 (4). Atomic displacement parameters of S1 and O3 were restrained using a DELU command.
details are summarized in Table 2Structural data
CCDC reference: 1971616
https://doi.org/10.1107/S2414314620010287/bt4093sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620010287/bt4093Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620010287/bt4093Isup3.cml
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).C21H15FN2O4S | F(000) = 848 |
Mr = 410.41 | Dx = 1.481 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8726 (4) Å | Cell parameters from 3064 reflections |
b = 15.8054 (7) Å | θ = 4.9–54.4° |
c = 11.8345 (4) Å | µ = 0.22 mm−1 |
β = 94.679 (1)° | T = 292 K |
V = 1840.51 (13) Å3 | Prismatic, colorless |
Z = 4 | 0.18 × 0.15 × 0.10 mm |
Bruker APEXII CCD diffractometer | 2580 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.030 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 26.0°, θmin = 2.9° |
Tmin = 0.671, Tmax = 0.746 | h = −12→12 |
9057 measured reflections | k = −19→16 |
3596 independent reflections | l = −13→14 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0419P)2 + 0.4204P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.21 e Å−3 |
3596 reflections | Δρmin = −0.23 e Å−3 |
351 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.022 (2) |
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. The position of H(2) atom was found from the diagram of differential Fourier synthesis. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.37546 (9) | 0.45878 (11) | 0.17560 (7) | 0.0574 (4) | 0.933 (4) |
O2 | 0.2617 (2) | 0.39173 (17) | 0.13707 (18) | 0.0585 (7) | 0.933 (4) |
O4 | 0.3356 (2) | 0.53877 (14) | 0.12761 (16) | 0.0804 (8) | 0.933 (4) |
O3 | 0.50142 (19) | 0.42592 (16) | 0.15129 (17) | 0.0930 (8) | |
S1' | 0.3792 (17) | 0.4087 (16) | 0.1887 (14) | 0.079 (5) | 0.067 (4) |
O2' | 0.251 (4) | 0.452 (3) | 0.118 (3) | 0.075 (11) | 0.067 (4) |
O4' | 0.373 (3) | 0.3271 (18) | 0.191 (2) | 0.076 (11) | 0.067 (4) |
F1 | 0.13032 (11) | 0.39571 (8) | 0.51531 (10) | 0.0450 (4) | |
O1 | 0.40253 (15) | 0.45785 (9) | 0.58419 (12) | 0.0448 (4) | |
N1 | 0.45048 (16) | 0.32572 (11) | 0.51448 (13) | 0.0363 (4) | |
N2 | 0.36500 (19) | 0.45557 (12) | 0.31047 (15) | 0.0437 (5) | |
C1 | 0.37823 (19) | 0.26508 (13) | 0.44351 (16) | 0.0339 (5) | |
C2 | 0.4208 (2) | 0.18520 (14) | 0.41621 (18) | 0.0410 (5) | |
C3 | 0.3295 (2) | 0.13620 (15) | 0.3496 (2) | 0.0486 (6) | |
C4 | 0.2019 (3) | 0.16596 (15) | 0.3120 (2) | 0.0499 (6) | |
C5 | 0.1611 (2) | 0.24676 (14) | 0.34049 (18) | 0.0412 (5) | |
C6 | 0.25100 (19) | 0.29646 (13) | 0.40678 (16) | 0.0344 (5) | |
C7 | 0.24062 (19) | 0.38483 (13) | 0.45012 (16) | 0.0332 (5) | |
C8 | 0.37284 (19) | 0.39541 (14) | 0.52730 (16) | 0.0347 (5) | |
C9 | 0.59230 (19) | 0.31952 (13) | 0.55089 (17) | 0.0368 (5) | |
C10 | 0.6346 (2) | 0.31418 (17) | 0.66367 (19) | 0.0522 (6) | |
C11 | 0.7729 (3) | 0.31052 (19) | 0.6958 (2) | 0.0633 (8) | |
C12 | 0.8648 (3) | 0.31018 (17) | 0.6165 (2) | 0.0564 (7) | |
C13 | 0.8220 (2) | 0.31587 (18) | 0.5039 (2) | 0.0588 (7) | |
C14 | 0.6849 (2) | 0.32088 (17) | 0.4702 (2) | 0.0512 (6) | |
C15 | 0.2332 (2) | 0.45561 (14) | 0.36026 (17) | 0.0361 (5) | |
C16 | 0.1135 (2) | 0.44411 (13) | 0.27349 (18) | 0.0383 (5) | |
C17 | −0.0177 (2) | 0.45994 (15) | 0.3006 (2) | 0.0505 (6) | |
C18 | −0.1280 (3) | 0.44404 (17) | 0.2237 (3) | 0.0631 (8) | |
C19 | −0.1082 (3) | 0.41453 (19) | 0.1173 (3) | 0.0696 (8) | |
C20 | 0.0215 (3) | 0.39940 (19) | 0.0871 (2) | 0.0664 (8) | |
C21 | 0.1298 (2) | 0.41352 (15) | 0.16628 (19) | 0.0490 (6) | |
H1 | 0.2197 (19) | 0.5066 (14) | 0.3987 (17) | 0.037 (5)* | |
H2 | 0.651 (2) | 0.3249 (15) | 0.393 (2) | 0.060 (7)* | |
H3 | 0.071 (2) | 0.2662 (13) | 0.3161 (16) | 0.040 (6)* | |
H4 | 0.508 (2) | 0.1655 (13) | 0.4453 (16) | 0.040 (6)* | |
H5 | 0.357 (2) | 0.0802 (15) | 0.3293 (18) | 0.049 (6)* | |
H6 | 0.803 (3) | 0.3077 (17) | 0.774 (2) | 0.078 (8)* | |
H8 | −0.217 (3) | 0.4545 (17) | 0.244 (2) | 0.080 (9)* | |
H9 | 0.137 (2) | 0.1290 (16) | 0.266 (2) | 0.061 (7)* | |
H10 | 0.887 (3) | 0.3167 (17) | 0.447 (2) | 0.075 (8)* | |
H11 | 0.962 (3) | 0.3091 (16) | 0.642 (2) | 0.074 (8)* | |
H12 | 0.427 (3) | 0.4894 (16) | 0.346 (2) | 0.065 (8)* | |
H13 | −0.183 (3) | 0.4066 (19) | 0.062 (2) | 0.090 (9)* | |
H14 | −0.032 (2) | 0.4815 (16) | 0.374 (2) | 0.066 (8)* | |
H15 | 0.568 (2) | 0.3155 (15) | 0.716 (2) | 0.062 (7)* | |
H17 | 0.044 (3) | 0.3776 (17) | 0.015 (2) | 0.078 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0534 (5) | 0.0792 (9) | 0.0403 (4) | −0.0260 (5) | 0.0085 (3) | −0.0133 (5) |
O2 | 0.0526 (13) | 0.0712 (17) | 0.0521 (12) | −0.0169 (13) | 0.0062 (10) | −0.0275 (12) |
O4 | 0.0994 (17) | 0.0848 (17) | 0.0546 (12) | −0.0396 (13) | −0.0075 (11) | 0.0232 (11) |
O3 | 0.0565 (12) | 0.148 (2) | 0.0774 (13) | −0.0243 (13) | 0.0253 (10) | −0.0428 (14) |
S1' | 0.090 (8) | 0.065 (12) | 0.087 (10) | −0.045 (9) | 0.042 (8) | −0.014 (8) |
O2' | 0.08 (2) | 0.09 (3) | 0.052 (17) | 0.03 (2) | −0.006 (14) | 0.014 (18) |
O4' | 0.11 (3) | 0.046 (18) | 0.08 (2) | −0.015 (16) | 0.025 (17) | 0.000 (14) |
F1 | 0.0324 (7) | 0.0573 (8) | 0.0462 (7) | 0.0019 (6) | 0.0095 (5) | −0.0056 (6) |
O1 | 0.0440 (9) | 0.0443 (9) | 0.0449 (8) | −0.0035 (7) | −0.0032 (7) | −0.0136 (7) |
N1 | 0.0284 (9) | 0.0409 (10) | 0.0387 (9) | 0.0014 (8) | −0.0017 (7) | −0.0056 (8) |
N2 | 0.0416 (11) | 0.0496 (12) | 0.0398 (10) | −0.0153 (9) | 0.0023 (8) | −0.0045 (9) |
C1 | 0.0319 (10) | 0.0379 (12) | 0.0319 (10) | −0.0037 (9) | 0.0027 (8) | −0.0028 (9) |
C2 | 0.0370 (12) | 0.0399 (13) | 0.0458 (12) | 0.0033 (10) | 0.0023 (9) | −0.0013 (10) |
C3 | 0.0546 (15) | 0.0343 (13) | 0.0560 (14) | 0.0024 (11) | −0.0001 (11) | −0.0080 (11) |
C4 | 0.0523 (15) | 0.0365 (13) | 0.0585 (14) | −0.0045 (11) | −0.0094 (11) | −0.0091 (11) |
C5 | 0.0358 (12) | 0.0388 (13) | 0.0474 (12) | −0.0027 (10) | −0.0061 (10) | −0.0038 (10) |
C6 | 0.0310 (10) | 0.0358 (12) | 0.0363 (10) | −0.0006 (9) | 0.0016 (8) | 0.0006 (9) |
C7 | 0.0274 (10) | 0.0368 (12) | 0.0356 (10) | −0.0001 (8) | 0.0039 (8) | −0.0063 (9) |
C8 | 0.0315 (11) | 0.0425 (13) | 0.0302 (10) | −0.0035 (9) | 0.0027 (8) | −0.0034 (9) |
C9 | 0.0285 (10) | 0.0408 (13) | 0.0405 (11) | −0.0007 (9) | −0.0012 (8) | −0.0002 (10) |
C10 | 0.0428 (13) | 0.0735 (18) | 0.0399 (12) | 0.0008 (12) | −0.0002 (10) | 0.0076 (12) |
C11 | 0.0528 (16) | 0.083 (2) | 0.0511 (15) | 0.0011 (14) | −0.0157 (13) | 0.0125 (15) |
C12 | 0.0349 (13) | 0.0544 (16) | 0.0777 (18) | 0.0001 (11) | −0.0087 (12) | 0.0057 (13) |
C13 | 0.0360 (13) | 0.0709 (19) | 0.0704 (17) | −0.0016 (12) | 0.0094 (12) | 0.0001 (15) |
C14 | 0.0384 (13) | 0.0725 (18) | 0.0426 (13) | −0.0039 (12) | 0.0025 (10) | −0.0009 (12) |
C15 | 0.0377 (12) | 0.0318 (12) | 0.0384 (11) | −0.0001 (9) | 0.0005 (9) | −0.0067 (9) |
C16 | 0.0398 (12) | 0.0289 (12) | 0.0446 (12) | −0.0013 (9) | −0.0058 (9) | 0.0012 (9) |
C17 | 0.0475 (14) | 0.0420 (14) | 0.0605 (16) | 0.0092 (11) | −0.0047 (12) | 0.0008 (12) |
C18 | 0.0441 (15) | 0.0549 (17) | 0.087 (2) | 0.0062 (13) | −0.0149 (14) | 0.0103 (15) |
C19 | 0.0598 (19) | 0.0663 (19) | 0.077 (2) | −0.0114 (15) | −0.0303 (16) | 0.0128 (16) |
C20 | 0.072 (2) | 0.072 (2) | 0.0518 (15) | −0.0189 (16) | −0.0151 (14) | −0.0037 (14) |
C21 | 0.0480 (14) | 0.0524 (15) | 0.0458 (13) | −0.0107 (11) | −0.0023 (10) | −0.0028 (11) |
S1—O3 | 1.399 (2) | C6—C7 | 1.494 (3) |
S1—O4 | 1.428 (3) | C7—C8 | 1.540 (3) |
S1—O2 | 1.584 (2) | C7—C15 | 1.541 (3) |
S1—N2 | 1.6086 (19) | C9—C10 | 1.368 (3) |
O2—C21 | 1.417 (3) | C9—C14 | 1.375 (3) |
O3—S1' | 1.346 (14) | C10—C11 | 1.389 (3) |
S1'—O4' | 1.29 (4) | C10—H15 | 0.94 (2) |
S1'—O2' | 1.62 (4) | C11—C12 | 1.358 (4) |
S1'—N2 | 1.636 (16) | C11—H6 | 0.95 (3) |
O2'—C21 | 1.50 (4) | C12—C13 | 1.367 (4) |
F1—C7 | 1.396 (2) | C12—H11 | 0.98 (3) |
O1—C8 | 1.217 (2) | C13—C14 | 1.382 (3) |
N1—C8 | 1.357 (3) | C13—H10 | 0.97 (3) |
N1—C1 | 1.427 (2) | C14—H2 | 0.95 (2) |
N1—C9 | 1.434 (2) | C15—C16 | 1.513 (3) |
N2—C15 | 1.471 (3) | C15—H1 | 0.94 (2) |
N2—H12 | 0.89 (3) | C16—C21 | 1.380 (3) |
C1—C2 | 1.377 (3) | C16—C17 | 1.382 (3) |
C1—C6 | 1.387 (3) | C17—C18 | 1.383 (3) |
C2—C3 | 1.385 (3) | C17—H14 | 0.96 (3) |
C2—H4 | 0.95 (2) | C18—C19 | 1.372 (4) |
C3—C4 | 1.383 (3) | C18—H8 | 0.94 (3) |
C3—H5 | 0.96 (2) | C19—C20 | 1.378 (4) |
C4—C5 | 1.389 (3) | C19—H13 | 0.96 (3) |
C4—H9 | 0.99 (2) | C20—C21 | 1.382 (3) |
C5—C6 | 1.381 (3) | C20—H17 | 0.97 (3) |
C5—H3 | 0.96 (2) | ||
O3—S1—O4 | 117.89 (16) | O1—C8—C7 | 124.78 (18) |
O3—S1—O2 | 108.28 (17) | N1—C8—C7 | 107.73 (16) |
O4—S1—O2 | 108.17 (16) | C10—C9—C14 | 120.7 (2) |
O3—S1—N2 | 108.81 (13) | C10—C9—N1 | 120.65 (18) |
O4—S1—N2 | 112.62 (14) | C14—C9—N1 | 118.59 (18) |
O2—S1—N2 | 99.39 (13) | C9—C10—C11 | 119.0 (2) |
C21—O2—S1 | 114.28 (18) | C9—C10—H15 | 117.9 (15) |
O4'—S1'—O3 | 105 (2) | C11—C10—H15 | 123.1 (15) |
O4'—S1'—O2' | 114 (3) | C12—C11—C10 | 120.6 (2) |
O3—S1'—O2' | 115 (2) | C12—C11—H6 | 119.8 (16) |
O4'—S1'—N2 | 115.1 (18) | C10—C11—H6 | 119.6 (16) |
O3—S1'—N2 | 110.0 (11) | C11—C12—C13 | 120.2 (2) |
O2'—S1'—N2 | 98.2 (19) | C11—C12—H11 | 118.4 (15) |
C21—O2'—S1' | 104 (2) | C13—C12—H11 | 121.3 (15) |
C8—N1—C1 | 110.56 (16) | C12—C13—C14 | 120.2 (2) |
C8—N1—C9 | 124.62 (17) | C12—C13—H10 | 121.0 (16) |
C1—N1—C9 | 124.05 (16) | C14—C13—H10 | 118.9 (16) |
C15—N2—S1 | 121.86 (15) | C9—C14—C13 | 119.3 (2) |
C15—N2—S1' | 119.7 (6) | C9—C14—H2 | 117.8 (14) |
C15—N2—H12 | 114.1 (17) | C13—C14—H2 | 122.8 (14) |
S1—N2—H12 | 110.6 (17) | N2—C15—C16 | 113.32 (17) |
S1'—N2—H12 | 125.5 (18) | N2—C15—C7 | 106.41 (16) |
C2—C1—C6 | 122.69 (19) | C16—C15—C7 | 111.82 (17) |
C2—C1—N1 | 127.34 (18) | N2—C15—H1 | 111.1 (12) |
C6—C1—N1 | 109.93 (17) | C16—C15—H1 | 107.3 (12) |
C1—C2—C3 | 116.7 (2) | C7—C15—H1 | 106.8 (12) |
C1—C2—H4 | 119.9 (12) | C21—C16—C17 | 117.3 (2) |
C3—C2—H4 | 123.3 (12) | C21—C16—C15 | 121.5 (2) |
C4—C3—C2 | 121.7 (2) | C17—C16—C15 | 121.1 (2) |
C4—C3—H5 | 120.3 (13) | C16—C17—C18 | 121.1 (3) |
C2—C3—H5 | 117.9 (13) | C16—C17—H14 | 119.1 (15) |
C3—C4—C5 | 120.6 (2) | C18—C17—H14 | 119.8 (15) |
C3—C4—H9 | 120.2 (14) | C19—C18—C17 | 120.1 (3) |
C5—C4—H9 | 119.2 (14) | C19—C18—H8 | 120.0 (18) |
C6—C5—C4 | 118.4 (2) | C17—C18—H8 | 119.9 (18) |
C6—C5—H3 | 121.6 (12) | C18—C19—C20 | 120.2 (3) |
C4—C5—H3 | 120.0 (12) | C18—C19—H13 | 120.7 (18) |
C5—C6—C1 | 119.89 (19) | C20—C19—H13 | 119.0 (18) |
C5—C6—C7 | 131.90 (19) | C19—C20—C21 | 118.7 (3) |
C1—C6—C7 | 108.20 (17) | C19—C20—H17 | 125.3 (16) |
F1—C7—C6 | 112.54 (15) | C21—C20—H17 | 116.0 (16) |
F1—C7—C8 | 108.70 (14) | C16—C21—C20 | 122.6 (2) |
C6—C7—C8 | 103.09 (16) | C16—C21—O2 | 119.2 (2) |
F1—C7—C15 | 107.28 (15) | C20—C21—O2 | 118.1 (2) |
C6—C7—C15 | 116.26 (16) | C16—C21—O2' | 111.3 (15) |
C8—C7—C15 | 108.69 (16) | C20—C21—O2' | 113.9 (12) |
O1—C8—N1 | 127.38 (18) | ||
O3—S1—O2—C21 | 174.48 (19) | C1—N1—C9—C10 | −119.0 (2) |
O4—S1—O2—C21 | −56.7 (2) | C8—N1—C9—C14 | −106.6 (2) |
N2—S1—O2—C21 | 61.0 (3) | C1—N1—C9—C14 | 62.4 (3) |
O4'—S1'—O2'—C21 | 51 (3) | C14—C9—C10—C11 | 0.3 (4) |
O3—S1'—O2'—C21 | 172.2 (14) | N1—C9—C10—C11 | −178.3 (2) |
N2—S1'—O2'—C21 | −71 (3) | C9—C10—C11—C12 | −1.6 (4) |
O3—S1—N2—C15 | −157.38 (18) | C10—C11—C12—C13 | 1.9 (4) |
O4—S1—N2—C15 | 70.0 (2) | C11—C12—C13—C14 | −0.9 (4) |
O2—S1—N2—C15 | −44.3 (2) | C10—C9—C14—C13 | 0.7 (4) |
O4'—S1'—N2—C15 | −70 (2) | N1—C9—C14—C13 | 179.3 (2) |
O3—S1'—N2—C15 | 171.6 (11) | C12—C13—C14—C9 | −0.4 (4) |
O2'—S1'—N2—C15 | 51 (2) | S1—N2—C15—C16 | 9.7 (3) |
C8—N1—C1—C2 | −176.2 (2) | S1'—N2—C15—C16 | −23.9 (11) |
C9—N1—C1—C2 | 13.4 (3) | S1—N2—C15—C7 | 132.95 (18) |
C8—N1—C1—C6 | 1.3 (2) | S1'—N2—C15—C7 | 99.4 (11) |
C9—N1—C1—C6 | −169.02 (17) | F1—C7—C15—N2 | 167.10 (15) |
C6—C1—C2—C3 | −0.2 (3) | C6—C7—C15—N2 | −66.0 (2) |
N1—C1—C2—C3 | 177.03 (19) | C8—C7—C15—N2 | 49.7 (2) |
C1—C2—C3—C4 | 0.1 (3) | F1—C7—C15—C16 | −68.7 (2) |
C2—C3—C4—C5 | 0.0 (4) | C6—C7—C15—C16 | 58.3 (2) |
C3—C4—C5—C6 | 0.1 (3) | C8—C7—C15—C16 | 173.96 (16) |
C4—C5—C6—C1 | −0.2 (3) | N2—C15—C16—C21 | 16.9 (3) |
C4—C5—C6—C7 | 178.8 (2) | C7—C15—C16—C21 | −103.4 (2) |
C2—C1—C6—C5 | 0.3 (3) | N2—C15—C16—C17 | −166.4 (2) |
N1—C1—C6—C5 | −177.37 (18) | C7—C15—C16—C17 | 73.3 (3) |
C2—C1—C6—C7 | −178.93 (18) | C21—C16—C17—C18 | 1.3 (4) |
N1—C1—C6—C7 | 3.4 (2) | C15—C16—C17—C18 | −175.6 (2) |
C5—C6—C7—F1 | 57.8 (3) | C16—C17—C18—C19 | −2.1 (4) |
C1—C6—C7—F1 | −123.05 (17) | C17—C18—C19—C20 | 1.0 (4) |
C5—C6—C7—C8 | 174.7 (2) | C18—C19—C20—C21 | 0.8 (4) |
C1—C6—C7—C8 | −6.1 (2) | C17—C16—C21—C20 | 0.6 (4) |
C5—C6—C7—C15 | −66.5 (3) | C15—C16—C21—C20 | 177.4 (2) |
C1—C6—C7—C15 | 112.66 (19) | C17—C16—C21—O2 | −176.3 (2) |
C1—N1—C8—O1 | 178.27 (19) | C15—C16—C21—O2 | 0.5 (3) |
C9—N1—C8—O1 | −11.5 (3) | C17—C16—C21—O2' | 140.5 (14) |
C1—N1—C8—C7 | −5.3 (2) | C15—C16—C21—O2' | −42.6 (14) |
C9—N1—C8—C7 | 165.00 (16) | C19—C20—C21—C16 | −1.6 (4) |
F1—C7—C8—O1 | −56.9 (2) | C19—C20—C21—O2 | 175.3 (3) |
C6—C7—C8—O1 | −176.50 (18) | C19—C20—C21—O2' | −140.6 (17) |
C15—C7—C8—O1 | 59.6 (2) | S1—O2—C21—C16 | −44.5 (3) |
F1—C7—C8—N1 | 126.54 (17) | S1—O2—C21—C20 | 138.4 (2) |
C6—C7—C8—N1 | 6.9 (2) | S1'—O2'—C21—C16 | 73 (2) |
C15—C7—C8—N1 | −117.00 (18) | S1'—O2'—C21—C20 | −143.7 (16) |
C8—N1—C9—C10 | 72.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H12···O1i | 0.89 (3) | 1.99 (3) | 2.868 (2) | 166 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Funding information
Financial support by the Students Innovation Program of Shanghai University of Engineering Science (cs1604002) is gratefully acknowledged.
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