organic compounds
N-[(1R,2S)-1-(4-Bromophenyl)-2-fluoro-3-(2-methylphenyl)-3-oxopropyl]-4-nitrobenzamide
aDepartment of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
*Correspondence e-mail: ya.li@sues.edu.cn
The title compound, C23H18BrFN2O4, contains two chiral carbon centres and the has been confirmed as (1R,2S). The dihedral angles between the three phenyl rings are 12.4 (4), 34.2 (4) and 44.5 (4)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains, which which are further connected by C—H⋯O interactions, generating a three dimensional network structure.
Keywords: crystal structure; amine; fluorine; amide; ketone.
CCDC reference: 1831032
Structure description
Fluorine is highly important in medicinal chemistry (Wang et al., 2014). The introduction of fluorine into a bioactive molecule often improves the binding affinity, metabolic stability, and bioavailability (Purser et al., 2008). In this context, the β-fluoroamine motif is an important structural motif and has been found in a number of drug candidates (Murray et al., 2003; Li et al., 2016). It is generally believed that a β-fluoro substitution lowers the pKa value of the neighboring and can thus modulate many pharmacological properties (Morgenthaler et al., 2007).
In the title compound (Fig. 1), the fluoro and amino substituents adopt an anti configuration and the of the two chiral carbon centres, C8 and C9, has been determined as (1R,2S). In the crystal, molecules are linked by classical N—H⋯O hydrogen bonds (Table 1, Fig. 2) into [001] chains, which which are further connected by C—H⋯O interactions, generating a three-dimensional network structure.
Synthesis and crystallization
Sodium bis(trimethylsilyl)amide (NaHMDS, 1.5 ml, 1.0 mol/l in THF) was added to a solution of 2-fluoro-1-(o-tolyl)ethan-1-one (228 mg, 1.5 mmol), (RS)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide (288 mg, 1.0 mmol) and Et2O (4 ml) at 203 K. The reaction mixture was stirred for 30 min, followed by a routine work-up to give the crude condensation intermediate. Without further purification, the crude intermediate was dissolved in 5 mL HCl/MeOH (4 mol l−1) at room temperature and the mixture was stirred for 20 min. The volatile materials were removed under vacuum, followed by the addition of 4-nitrobenzoyl chloride (184 mg, 1.0 mmol), NEt3 (202 mg, 2.0 mmol) and THF (3.0 mL). After 3 h, H2O (5 ml) was added, and the quenched reaction mixture was extracted with ethyl acetate (3 × 20 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent under vacuum was followed by flash to give the title compound (218 mg, 45%). The resulting compound was recrystallized from ethyl acetate/hexane (1:2) to give colourless crystals.
1H NMR (400 MHz, CDCl3) δ = 8.33 (d, J = 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H), 7.48–7.54 (m, 4H), 7.28–7.34 (m, 4H), 7.21 (d, J = 8.0 Hz, 1H), 5.88 (dd, J = 48.0, 4.0 Hz, 1H), 5.74 (dd, J = 24.0, 8.0 Hz, 1H), 2.38 (s, 3H).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1831032
https://doi.org/10.1107/S2414314618004595/ff4026sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004595/ff4026Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004595/ff4026Isup3.cml
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H18BrFN2O4 | Dx = 1.524 Mg m−3 |
Mr = 485.30 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P21212 | Cell parameters from 1711 reflections |
a = 18.883 (3) Å | θ = 4.7–39.6° |
b = 21.006 (3) Å | µ = 1.99 mm−1 |
c = 5.3312 (8) Å | T = 293 K |
V = 2114.6 (5) Å3 | Prismatic, colorless |
Z = 4 | 0.22 × 0.14 × 0.10 mm |
F(000) = 984 |
Bruker SMART CCD area detector diffractometer | 2701 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.048 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | θmax = 25.0°, θmin = 1.5° |
Tmin = 0.528, Tmax = 0.746 | h = −22→21 |
17885 measured reflections | k = −20→24 |
3736 independent reflections | l = −6→6 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.0302P)2 + 2.9914P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.33 e Å−3 |
3736 reflections | Δρmin = −0.35 e Å−3 |
285 parameters | Absolute structure: Flack x determined using 848 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.008 (19) |
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 | 0.36145 (6) | 0.99683 (5) | 0.9915 (3) | 0.1162 (5) | |
F1 | 0.1370 (2) | 0.7403 (3) | 1.2524 (9) | 0.0816 (15) | |
N1 | 0.2301 (4) | 0.6919 (4) | 0.9107 (14) | 0.0550 (17) | |
N2 | 0.4240 (5) | 0.4409 (4) | 1.008 (3) | 0.106 (3) | |
O1 | 0.0800 (3) | 0.6433 (3) | 1.0115 (15) | 0.0865 (18) | |
O2 | 0.2587 (3) | 0.6735 (3) | 0.5099 (13) | 0.0710 (15) | |
O3 | 0.4463 (5) | 0.4374 (5) | 1.221 (3) | 0.149 (4) | |
O4 | 0.4313 (6) | 0.3998 (4) | 0.858 (2) | 0.167 (5) | |
C1 | −0.0043 (5) | 0.7710 (4) | 0.6813 (16) | 0.071 (2) | |
H1 | 0.0117 | 0.8031 | 0.7874 | 0.085* | |
C2 | −0.0520 (4) | 0.7856 (5) | 0.497 (2) | 0.085 (3) | |
H2 | −0.0678 | 0.8273 | 0.4773 | 0.102* | |
C3 | −0.0764 (5) | 0.7387 (6) | 0.343 (2) | 0.087 (3) | |
H3 | −0.1097 | 0.7480 | 0.2200 | 0.104* | |
C4 | −0.0519 (5) | 0.6781 (5) | 0.370 (2) | 0.082 (3) | |
H4 | −0.0684 | 0.6467 | 0.2620 | 0.098* | |
C5 | −0.0032 (4) | 0.6617 (4) | 0.5536 (15) | 0.064 (2) | |
C6 | 0.0211 (3) | 0.7095 (4) | 0.7142 (15) | 0.0513 (19) | |
C7 | 0.0723 (4) | 0.6953 (4) | 0.9182 (16) | 0.058 (2) | |
C8 | 0.1210 (3) | 0.7495 (4) | 1.0053 (16) | 0.0534 (16) | |
H8 | 0.0968 | 0.7904 | 0.9845 | 0.064* | |
C9 | 0.1898 (4) | 0.7495 (3) | 0.8539 (13) | 0.0465 (17) | |
H9 | 0.1771 | 0.7480 | 0.6758 | 0.056* | |
C10 | 0.2325 (4) | 0.8094 (3) | 0.8961 (14) | 0.0474 (18) | |
C11 | 0.2781 (4) | 0.8167 (4) | 1.0955 (16) | 0.062 (2) | |
H11 | 0.2834 | 0.7840 | 1.2116 | 0.075* | |
C12 | 0.3163 (5) | 0.8729 (5) | 1.1241 (18) | 0.076 (3) | |
H12 | 0.3471 | 0.8776 | 1.2589 | 0.091* | |
C13 | 0.3085 (4) | 0.9206 (4) | 0.955 (2) | 0.073 (3) | |
C14 | 0.2650 (5) | 0.9136 (4) | 0.757 (2) | 0.081 (3) | |
H14 | 0.2607 | 0.9462 | 0.6395 | 0.097* | |
C15 | 0.2266 (4) | 0.8581 (4) | 0.7278 (19) | 0.071 (2) | |
H15 | 0.1963 | 0.8538 | 0.5913 | 0.085* | |
C16 | 0.0228 (6) | 0.5939 (4) | 0.564 (2) | 0.114 (4) | |
H16A | 0.0056 | 0.5710 | 0.4210 | 0.170* | |
H16B | 0.0056 | 0.5740 | 0.7148 | 0.170* | |
H16C | 0.0736 | 0.5935 | 0.5646 | 0.170* | |
C17 | 0.2622 (4) | 0.6593 (4) | 0.7316 (17) | 0.0533 (19) | |
C18 | 0.3041 (4) | 0.6024 (3) | 0.8126 (16) | 0.055 (2) | |
C19 | 0.3049 (5) | 0.5494 (4) | 0.663 (2) | 0.083 (3) | |
H19 | 0.2786 | 0.5489 | 0.5153 | 0.100* | |
C20 | 0.3442 (6) | 0.4969 (5) | 0.727 (2) | 0.100 (3) | |
H20 | 0.3440 | 0.4609 | 0.6253 | 0.120* | |
C21 | 0.3828 (4) | 0.4981 (4) | 0.938 (2) | 0.076 (3) | |
C22 | 0.3846 (5) | 0.5492 (5) | 1.088 (2) | 0.087 (3) | |
H22 | 0.4126 | 0.5492 | 1.2312 | 0.104* | |
C23 | 0.3442 (4) | 0.6025 (4) | 1.026 (2) | 0.075 (3) | |
H23 | 0.3446 | 0.6381 | 1.1299 | 0.090* | |
H1A | 0.231 (3) | 0.683 (3) | 1.068 (15) | 0.035 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1014 (7) | 0.0852 (7) | 0.1621 (12) | −0.0295 (6) | 0.0183 (9) | −0.0316 (10) |
F1 | 0.063 (3) | 0.135 (5) | 0.047 (3) | 0.006 (3) | 0.002 (2) | −0.003 (3) |
N1 | 0.061 (4) | 0.065 (5) | 0.039 (4) | 0.016 (3) | 0.006 (3) | −0.002 (3) |
N2 | 0.099 (6) | 0.060 (6) | 0.160 (11) | 0.023 (5) | 0.035 (9) | 0.036 (8) |
O1 | 0.092 (4) | 0.072 (4) | 0.096 (5) | 0.005 (3) | −0.010 (5) | 0.024 (4) |
O2 | 0.085 (4) | 0.074 (4) | 0.053 (4) | 0.017 (3) | 0.002 (4) | −0.001 (4) |
O3 | 0.124 (7) | 0.131 (8) | 0.192 (12) | 0.057 (6) | 0.012 (8) | 0.065 (9) |
O4 | 0.218 (11) | 0.070 (6) | 0.212 (12) | 0.062 (7) | 0.062 (9) | 0.029 (7) |
C1 | 0.070 (5) | 0.070 (6) | 0.073 (6) | 0.012 (5) | −0.018 (5) | −0.010 (4) |
C2 | 0.080 (5) | 0.088 (6) | 0.088 (7) | 0.034 (5) | −0.019 (6) | −0.005 (7) |
C3 | 0.061 (5) | 0.119 (9) | 0.081 (7) | 0.017 (6) | −0.019 (5) | −0.009 (7) |
C4 | 0.066 (5) | 0.096 (8) | 0.083 (7) | −0.022 (5) | −0.016 (5) | −0.012 (6) |
C5 | 0.066 (4) | 0.063 (5) | 0.064 (6) | −0.016 (4) | 0.007 (5) | −0.001 (4) |
C6 | 0.040 (4) | 0.056 (5) | 0.058 (5) | 0.000 (3) | 0.002 (3) | 0.003 (4) |
C7 | 0.051 (4) | 0.057 (5) | 0.065 (6) | 0.008 (4) | 0.002 (4) | 0.002 (4) |
C8 | 0.054 (4) | 0.063 (4) | 0.044 (4) | 0.011 (3) | −0.009 (4) | −0.001 (4) |
C9 | 0.053 (4) | 0.049 (4) | 0.037 (4) | 0.006 (3) | −0.005 (3) | 0.000 (3) |
C10 | 0.050 (4) | 0.051 (4) | 0.042 (4) | 0.008 (3) | 0.004 (3) | −0.004 (3) |
C11 | 0.068 (5) | 0.062 (5) | 0.057 (6) | −0.003 (4) | −0.006 (4) | 0.004 (4) |
C12 | 0.066 (5) | 0.099 (7) | 0.063 (6) | −0.002 (5) | −0.004 (5) | −0.022 (6) |
C13 | 0.064 (5) | 0.072 (6) | 0.081 (7) | −0.005 (4) | 0.012 (5) | −0.009 (6) |
C14 | 0.096 (6) | 0.063 (6) | 0.084 (7) | 0.001 (5) | −0.004 (6) | 0.011 (5) |
C15 | 0.072 (5) | 0.068 (6) | 0.073 (6) | −0.001 (4) | −0.018 (5) | 0.008 (5) |
C16 | 0.162 (11) | 0.062 (6) | 0.117 (10) | −0.005 (6) | −0.027 (8) | −0.015 (6) |
C17 | 0.048 (4) | 0.053 (5) | 0.059 (6) | −0.005 (3) | 0.002 (4) | 0.000 (4) |
C18 | 0.054 (4) | 0.040 (4) | 0.070 (6) | −0.008 (3) | 0.012 (4) | 0.001 (4) |
C19 | 0.098 (7) | 0.048 (5) | 0.103 (8) | 0.005 (5) | −0.016 (6) | −0.011 (5) |
C20 | 0.129 (9) | 0.043 (5) | 0.129 (10) | 0.007 (6) | 0.005 (8) | −0.012 (7) |
C21 | 0.069 (5) | 0.051 (5) | 0.108 (9) | 0.011 (4) | 0.027 (5) | 0.015 (6) |
C22 | 0.074 (6) | 0.085 (7) | 0.103 (9) | 0.021 (5) | −0.001 (5) | 0.011 (6) |
C23 | 0.074 (5) | 0.060 (5) | 0.091 (7) | 0.014 (4) | −0.006 (6) | −0.012 (5) |
Br1—C13 | 1.897 (8) | C9—H9 | 0.9800 |
F1—C8 | 1.365 (9) | C10—C15 | 1.366 (11) |
N1—C17 | 1.323 (11) | C10—C11 | 1.377 (11) |
N1—C9 | 1.460 (9) | C11—C12 | 1.391 (12) |
N1—H1A | 0.86 (8) | C11—H11 | 0.9300 |
N2—O4 | 1.187 (16) | C12—C13 | 1.357 (13) |
N2—O3 | 1.209 (17) | C12—H12 | 0.9300 |
N2—C21 | 1.478 (12) | C13—C14 | 1.348 (14) |
O1—C7 | 1.209 (9) | C14—C15 | 1.382 (12) |
O2—C17 | 1.220 (10) | C14—H14 | 0.9300 |
C1—C2 | 1.369 (12) | C15—H15 | 0.9300 |
C1—C6 | 1.388 (11) | C16—H16A | 0.9600 |
C1—H1 | 0.9300 | C16—H16B | 0.9600 |
C2—C3 | 1.362 (13) | C16—H16C | 0.9600 |
C2—H2 | 0.9300 | C17—C18 | 1.497 (10) |
C3—C4 | 1.362 (13) | C18—C23 | 1.367 (12) |
C3—H3 | 0.9300 | C18—C19 | 1.372 (11) |
C4—C5 | 1.386 (12) | C19—C20 | 1.371 (13) |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.397 (10) | C20—C21 | 1.343 (14) |
C5—C16 | 1.507 (12) | C20—H20 | 0.9300 |
C6—C7 | 1.486 (11) | C21—C22 | 1.337 (14) |
C7—C8 | 1.535 (10) | C22—C23 | 1.395 (12) |
C8—C9 | 1.529 (10) | C22—H22 | 0.9300 |
C8—H8 | 0.9800 | C23—H23 | 0.9300 |
C9—C10 | 1.510 (10) | ||
C17—N1—C9 | 121.2 (7) | C10—C11—C12 | 120.3 (8) |
C17—N1—H1A | 125 (5) | C10—C11—H11 | 119.8 |
C9—N1—H1A | 114 (5) | C12—C11—H11 | 119.8 |
O4—N2—O3 | 123.2 (12) | C13—C12—C11 | 119.8 (9) |
O4—N2—C21 | 118.8 (15) | C13—C12—H12 | 120.1 |
O3—N2—C21 | 117.9 (13) | C11—C12—H12 | 120.1 |
C2—C1—C6 | 121.8 (8) | C14—C13—C12 | 120.4 (9) |
C2—C1—H1 | 119.1 | C14—C13—Br1 | 119.6 (8) |
C6—C1—H1 | 119.1 | C12—C13—Br1 | 119.9 (8) |
C3—C2—C1 | 119.5 (9) | C13—C14—C15 | 120.0 (9) |
C3—C2—H2 | 120.3 | C13—C14—H14 | 120.0 |
C1—C2—H2 | 120.3 | C15—C14—H14 | 120.0 |
C4—C3—C2 | 119.8 (9) | C10—C15—C14 | 121.1 (9) |
C4—C3—H3 | 120.1 | C10—C15—H15 | 119.4 |
C2—C3—H3 | 120.1 | C14—C15—H15 | 119.4 |
C3—C4—C5 | 122.2 (9) | C5—C16—H16A | 109.5 |
C3—C4—H4 | 118.9 | C5—C16—H16B | 109.5 |
C5—C4—H4 | 118.9 | H16A—C16—H16B | 109.5 |
C4—C5—C6 | 118.1 (8) | C5—C16—H16C | 109.5 |
C4—C5—C16 | 118.6 (9) | H16A—C16—H16C | 109.5 |
C6—C5—C16 | 123.3 (8) | H16B—C16—H16C | 109.5 |
C1—C6—C5 | 118.6 (7) | O2—C17—N1 | 123.3 (8) |
C1—C6—C7 | 120.2 (7) | O2—C17—C18 | 120.2 (8) |
C5—C6—C7 | 121.2 (7) | N1—C17—C18 | 116.6 (8) |
O1—C7—C6 | 124.1 (7) | C23—C18—C19 | 118.7 (8) |
O1—C7—C8 | 118.2 (7) | C23—C18—C17 | 122.1 (7) |
C6—C7—C8 | 117.6 (7) | C19—C18—C17 | 119.1 (8) |
F1—C8—C9 | 108.7 (5) | C20—C19—C18 | 120.9 (10) |
F1—C8—C7 | 108.6 (6) | C20—C19—H19 | 119.5 |
C9—C8—C7 | 110.5 (6) | C18—C19—H19 | 119.5 |
F1—C8—H8 | 109.7 | C21—C20—C19 | 119.3 (10) |
C9—C8—H8 | 109.7 | C21—C20—H20 | 120.4 |
C7—C8—H8 | 109.7 | C19—C20—H20 | 120.4 |
N1—C9—C10 | 112.4 (6) | C22—C21—C20 | 121.8 (9) |
N1—C9—C8 | 109.4 (6) | C22—C21—N2 | 119.3 (12) |
C10—C9—C8 | 112.0 (6) | C20—C21—N2 | 118.9 (11) |
N1—C9—H9 | 107.6 | C21—C22—C23 | 119.5 (10) |
C10—C9—H9 | 107.6 | C21—C22—H22 | 120.3 |
C8—C9—H9 | 107.6 | C23—C22—H22 | 120.3 |
C15—C10—C11 | 118.3 (7) | C18—C23—C22 | 119.9 (9) |
C15—C10—C9 | 118.9 (7) | C18—C23—H23 | 120.1 |
C11—C10—C9 | 122.8 (7) | C22—C23—H23 | 120.1 |
C6—C1—C2—C3 | 0.9 (15) | C9—C10—C11—C12 | 179.7 (7) |
C1—C2—C3—C4 | −1.4 (16) | C10—C11—C12—C13 | 0.1 (13) |
C2—C3—C4—C5 | 1.1 (16) | C11—C12—C13—C14 | −1.2 (14) |
C3—C4—C5—C6 | −0.2 (14) | C11—C12—C13—Br1 | −179.3 (6) |
C3—C4—C5—C16 | −178.1 (10) | C12—C13—C14—C15 | 1.5 (15) |
C2—C1—C6—C5 | 0.0 (13) | Br1—C13—C14—C15 | 179.5 (7) |
C2—C1—C6—C7 | −179.3 (8) | C11—C10—C15—C14 | −0.5 (13) |
C4—C5—C6—C1 | −0.4 (11) | C9—C10—C15—C14 | −179.5 (8) |
C16—C5—C6—C1 | 177.4 (9) | C13—C14—C15—C10 | −0.6 (15) |
C4—C5—C6—C7 | 178.9 (8) | C9—N1—C17—O2 | −2.3 (12) |
C16—C5—C6—C7 | −3.3 (12) | C9—N1—C17—C18 | 177.8 (6) |
C1—C6—C7—O1 | 155.6 (9) | O2—C17—C18—C23 | 140.8 (8) |
C5—C6—C7—O1 | −23.7 (12) | N1—C17—C18—C23 | −39.3 (10) |
C1—C6—C7—C8 | −27.8 (10) | O2—C17—C18—C19 | −36.2 (11) |
C5—C6—C7—C8 | 152.9 (7) | N1—C17—C18—C19 | 143.7 (9) |
O1—C7—C8—F1 | −32.7 (10) | C23—C18—C19—C20 | 1.2 (14) |
C6—C7—C8—F1 | 150.5 (6) | C17—C18—C19—C20 | 178.3 (9) |
O1—C7—C8—C9 | 86.5 (9) | C18—C19—C20—C21 | −0.8 (16) |
C6—C7—C8—C9 | −90.3 (7) | C19—C20—C21—C22 | −0.5 (16) |
C17—N1—C9—C10 | −97.0 (8) | C19—C20—C21—N2 | 179.0 (9) |
C17—N1—C9—C8 | 137.8 (7) | O4—N2—C21—C22 | −168.2 (10) |
F1—C8—C9—N1 | 52.9 (8) | O3—N2—C21—C22 | 14.7 (15) |
C7—C8—C9—N1 | −66.3 (8) | O4—N2—C21—C20 | 12.3 (14) |
F1—C8—C9—C10 | −72.5 (7) | O3—N2—C21—C20 | −164.8 (11) |
C7—C8—C9—C10 | 168.4 (6) | C20—C21—C22—C23 | 1.3 (15) |
N1—C9—C10—C15 | 139.4 (7) | N2—C21—C22—C23 | −178.1 (8) |
C8—C9—C10—C15 | −96.9 (8) | C19—C18—C23—C22 | −0.3 (13) |
N1—C9—C10—C11 | −39.5 (9) | C17—C18—C23—C22 | −177.3 (8) |
C8—C9—C10—C11 | 84.2 (8) | C21—C22—C23—C18 | −0.9 (14) |
C15—C10—C11—C12 | 0.7 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···F1 | 0.86 (8) | 2.36 (6) | 2.728 (9) | 106 (5) |
N1—H1A···O2i | 0.86 (8) | 2.42 (8) | 3.263 (10) | 166 (4) |
C9—H9···F1ii | 0.98 | 2.39 | 3.364 (8) | 175 |
C8—H8···O4iii | 0.98 | 2.50 | 3.387 (12) | 150 |
C9—H9···O2 | 0.98 | 2.37 | 2.758 (9) | 103 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −x+1/2, y+1/2, −z+2. |
Funding information
The authors thank the Innovation Program of Shanghai University Students (cs1704003) for financial support.
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