N-[(1R,2S)-1-(4-Bromo­phen­yl)-2-fluoro-3-(2-methyl­phenyl)-3-oxoprop­yl]-4-nitro­benzamide

Luo, Y.; Feng, Y.; Zhang, X.; Zhang, J.; Chen, Y.-Y.; Li, Y.

doi:10.1107/S2414314618004595

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 3| March 2018| x180459

https://doi.org/10.1107/S2414314618004595

Open

access

N-[(1R,2S)-1-(4-Bromophenyl)-2-fluoro-3-(2-methylphenyl)-3-oxopropyl]-4-nitrobenzamide

Yu-hang Luo,^a Yan Feng,^a Xin-ran Zhang,^a Jin-rong Zhang,^a Yi-Yang Chen ^a and Ya Li ^a ^*

^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

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 6 March 2018; accepted 20 March 2018; online 23 March 2018)

The title compound, C₂₃H₁₈BrFN₂O₄, contains two chiral carbon centres and the absolute configuration 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 pK_a value of the neighboring amines, 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 absolute configuration 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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+2]$ .

Figure 1
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Intermolecular N—H⋯O interactions in the title compound, shown as dashed lines.

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 chromatography 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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₈BrFN₂O₄
M_r	485.30
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	18.883 (3), 21.006 (3), 5.3312 (8)
V (Å³)	2114.6 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.99
Crystal size (mm)	0.22 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.528, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	17885, 3736, 2701
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.150, 1.13
No. of reflections	3736
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.36
Absolute structure	Flack x determined using 848 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.008 (19)
Computer programs: SMART and SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008 ) and SHELXL2013 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1831032

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004595/ff4026sup1.cif

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

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: 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).

N-[(1R,2S)-1-(4-Bromophenyl)-2-fluoro-3-(2-methylphenyl)-3-oxopropyl]-4-nitrobenzamide top

Crystal data top

C₂₃H₁₈BrFN₂O₄	D_x = 1.524 Mg m⁻³
M_r = 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

Data collection top

Bruker SMART CCD area detector diffractometer	2701 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.048
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 25.0°, θ_min = 1.5°
T_min = 0.528, T_max = 0.746	h = −22→21
17885 measured reflections	k = −20→24
3736 independent reflections	l = −6→6

Refinement top

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(F_o²) + (0.0302P)² + 2.9914P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.150	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.33 e Å⁻³
3736 reflections	Δρ_min = −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)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y., Li, X., Shang, H., Chen, X. & Ren, X. (2016). J. Org. Chem. 81, 9858–9866. CSD CrossRef CAS Google Scholar
Morgenthaler, M., Schweizer, E., Hoffmann-Röder, A., Benini, F., Martin, R. E., Jaeschke, G., Wagner, B., Fischer, H., Bendels, S., Zimmerli, D., Schneider, J., Diederich, F., Kansy, M. & Müller, K. (2007). ChemMedChem, 2, 1100–1115. CrossRef CAS Google Scholar
Murray, T. K., Whalley, K., Robinson, C. S., Ward, M. A., Hicks, E., Lodge, D., Vandergriff, J. L., Baumbarger, P., Siuda, E., Gates, M., Ogden, A. M., Skolnick, P., Zimmerman, D. M., Nisenbaum, E. S., Bleakman, D. & O'Neill, M. J. (2003). J. Pharmacol. Exp. Ther. 306, 752–762. CrossRef CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. (2008). Chem. Soc. Rev. 37, 320–330. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wang, J., Sánchez-Roselló, M., Aceña, J. L., del Pozo, C., Sorochinsky, A. E., Fustero, S., Soloshonok, V. A. & Liu, H. (2014). Chem. Rev. 114, 2432–2506. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.