Crystal structure and Hirshfeld surface analysis of ethyl (3E)-5-(4-fluoro­phen­yl)3-{[(4-meth­oxy­phen­yl)formamido]­imino}-7-methyl-2H,3H,5H-[1,3]thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate 0.25-hydrate

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Alfayomy, A.M.; Ragab, F.A.F.; Abd ul-Malik, M.A.

doi:10.1107/S2056989022006041

research communications

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ISSN: 2056-9890

Volume 78| Part 9| September 2022| Pages 880-884

https://doi.org/10.1107/S2056989022006041

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Crystal structure and Hirshfeld surface analysis of ethyl (3E)-5-(4-fluorophenyl)3-{[(4-methoxyphenyl)formamido]imino}-7-methyl-2H,3H,5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 0.25-hydrate

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Abdallah M. Alfayomy,^e Fatma A. F. Ragab ^f and Mokhtar A. Abd ul-Malik ^g ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, 71524, Egypt, ^fDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, PO Box, 11562, Egypt, and ^gChemistry Department, Faculty of Applied Science, Taiz University, Taiz, Yemen
^*Correspondence e-mail: mokh.amin@taiz.edu.ye

Edited by M. Weil, Vienna University of Technology, Austria (Received 18 May 2022; accepted 7 June 2022; online 9 August 2022)

In the title compound, C₂₄H₂₃FN₄O₄S·0.25H₂O, the dihydropyrimidine ring is distinctly non-planar, with the flap C atom deviating by 0.297 (2) Å from the least-squares plane. In the crystal, zigzag chains are formed by N—H⋯N hydrogen bonds parallel to [010] and are connected into layers parallel to (100) by O—H⋯O, O—H⋯F, C—H⋯O, C—H⋯F and C—H⋯N hydrogen bonds. Additional C—H⋯O hydrogen bonds connect the layers into a three-dimensional network. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (42.6%), O⋯H/H⋯O (16.8%) and C⋯H/H⋯C (15.5%) contacts.

Keywords: crystal structure; pyrimidine; thiazole; hydrogen bond; Hirshfeld surface analysis.

CCDC reference: 2177565

1. Chemical context

Interest in the anticancer activities of dihydropyrimidines (DHPMs) has been increasing since 1999, when monastrol was discovered (Mayer et al., 1999 ; Leizerman et al., 2004 ). In addition, 1,3,4-oxadiazole has been reported to exhibit a significant anticancer activity (Yadagiri et al., 2015 ; Valente et al., 2014 ; El-Din et al., 2015 ). Since the combination of two or more pharmacophoric structural moieties can possibly augment the bioactivity, it was of interest to hybridize the DHPM moiety with 1,3,4-oxadiazole, hoping to discover potent anticancer agents.

In this context, a target compound was designed through the condensation of 6-methyl-4-aryl-1,2,3,4-tetrahydropyrimidine-2(1H)-thione derivatives and 2-(chloromethyl)-5-aryl-1,3,4-oxadiazole derivatives (Ragab et al., 2017 ). Unexpectedly, an intramolecular cyclization and ring opening of 1,3,4-oxadiazole occurred. The resulting product was chosen as an example of this series for further structural elucidation through X-ray crystallography. Herein we report the crystal structure and Hirshfeld analysis of the title compound, C₂₄H₂₃FN₄O₄S·0.25H₂O.

2. Structural commentary

In the title compound (Fig. 1), the dihydropyrimidine portion (N1/C3/C2/C1/N2/C4) of the central ring is planar to within 0.0286 (9) Å (r.m.s. deviation of the fitted atoms = 0.0211 Å), with the flap C1 atom being 0.297 (2) Å out of this plane towards the bonded 4-fluorophenyl group. A puckering analysis (Cremer & Pople, 1975 ) of this ring yielded the parameters Q = 0.2074 (15) Å, θ = 112.1 (4)° and φ = 3.5 (4)°. The dihedral angle between the C5–C10 phenyl ring and the least-squares plane of the dihydropyrimidine plane is 88.76 (5)°. The C4/N2/C15/C16/S1 ring is planar to within 0.0191 (8) Å (r.m.s. deviation of the fitted atoms = 0.0140 Å) and is inclined to the N1/C3/C2/C1/N2/C4 plane by 3.99 (9)°. The dihedral angle between the C4/N2/C15/C16/S1 ring and the C18–C23 phenyl ring is 9.28 (8)°.

Figure 1
The title molecule with the labelling scheme and displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features

In the crystal, molecules are connected into zigzag chains running parallel to [010] by N4—H4⋯N1 hydrogen bonds (Table 1). The chains are connected into (100) layers by O5—H5B⋯O3 and O5—H5A⋯F1 hydrogen bonds involving the water molecule, as well as by C13—H13B⋯F1, C16—H16A⋯N1 and all of the C—H⋯O hydrogen bonds listed in Table 1, except for the C24—H24C⋯O1 hydrogen bond (Figs. 2, 3 and 4) that serves to link the layers into a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1ⁱ	0.885 (19)	2.164 (19)	2.9888 (17)	154.8 (16)
C1—H1⋯O5ⁱⁱ	0.987 (17)	2.345 (18)	3.307 (5)	164.7 (13)
C7—H7⋯O4ⁱⁱⁱ	0.97 (2)	2.41 (2)	3.285 (2)	148.7 (17)
C13—H13B⋯F1ⁱⁱ	0.98 (3)	2.49 (3)	3.386 (2)	153.0 (19)
C16—H16A⋯N1ⁱ	0.98 (2)	2.58 (2)	3.4019 (19)	142.4 (15)
C16—H16B⋯O5^iv	0.98 (2)	2.37 (2)	3.282 (5)	154.6 (16)
C24—H24A⋯O1^v	0.99 (2)	2.53 (2)	3.450 (3)	154.6 (18)
C24—H24C⋯O1^vi	0.95 (2)	2.57 (2)	3.504 (2)	167.8 (17)
O5—H5A⋯F1	0.87	1.76	2.479 (5)	138
O5—H5B⋯O3^vii	0.87	2.00	2.863 (5)	174
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) ; (vi) ; (vii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
View of the molecular packing along [100]. O—H⋯O, O—H⋯F, C—H⋯ O, C—H⋯N and C—H⋯F hydrogen bonds are shown as dashed lines.

Figure 3
View of the molecular packing along [010]. Hydrogen bonds are depicted as in Fig. 2

Figure 4
View of the molecular packing along [001]. Hydrogen bonds are depicted as in Fig. 2

4. Hirshfeld surface analysis

A Hirshfeld surface analysis was performed, and two-dimensional fingerprint plots were constructed using Crystal Explorer17.5 to quantify the intermolecular interactions in the title molecule (Turner et al., 2017 ). Fig. 5 depicts the Hirshfeld surface plotted over d_norm in the range −0.7253 to +1.4745 arbitrary units, with red patches indicating putative hydrogen bonding in the crystal structure.

Figure 5
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm, with a fixed colour scale of −0.7253 (red) to +1.4745 (blue) a.u.

The intensity of the red patches is more pronounced for N4—H4⋯N1, C1—H1⋯O5, C16—H16B⋯O5, C24—H24A⋯O1, C24—H24C⋯O1 and O5—H5B⋯O3, thus revealing the strongest interactions when compared to other red spots on the Hirshfeld surface. Table 2 gives numerical data for close intermolecular contacts. The two-dimensional fingerprint plots (Fig. 6) shows that the largest contributions are from H⋯H (42.6%; Fig. 6b), O⋯H/H⋯O (16.8%; Fig. 6c) and C⋯H/H⋯C (15.5%; Fig. 6d) interactions. Other interactions contributing less to the crystal packing are from F⋯H/H⋯F (6.7%), N⋯H/H⋯N (4.5%), S⋯H/H⋯S (3.4%), S⋯C/C⋯S (3.4%), C⋯C (2.8%), S⋯N/N⋯S (1.4%),N⋯C/C⋯N (1.4%), O⋯C/C⋯O (0.7%), N⋯N (0.5%), O⋯N/N⋯O (0.2%) and S⋯O/O⋯S (0.1%) interactions.

Table 2
Summary of short interatomic contacts (Å) in the title compound.

Asterisks relate to atoms of the underoccupied water molecule.

Contact	Distance	Symmetry operation
N1⋯H4	2.165	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
F1⋯H13B	2.49	x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
F1⋯*H5A	1.76	x, y, z
F1⋯H14C	2.66	x, 1 + y, z
H14A⋯H24C	2.56	1 + x, −1 + y, z
H12C⋯O1	2.66	2 − x, 1 − y, 1 − z
H16B⋯O3	2.49	1 − x, 1 − y, 1 − z
O3⋯*H5B	2.00	x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
H7⋯O4	2.41	1 − x, 2 − y, 1 − z
H16B⋯*H5B	2.05	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H13A⋯H24B	2.41	1 + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
H14C⋯*O5	2.87	x, −1 + y, z

Figure 6
Two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) O⋯H/H⋯O and (d) C⋯H/H⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ) for compounds most closely related to the 2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine unit of the title compound gave the following hits: refcodes ZOWXAM (I) (Krishnamurthy et al., 2014 ); PONVOF (II) (Krishnamurthy & Begum, 2014 ); AFIZUM (III) (Fathima et al., 2013 ); YAYHAJ (IV) (Nagarajaiah et al., 2012 ); KUSQUL (V) (Jotani et al., 2010a ); PUJRIW (VI) (Jotani et al., 2010b ); DIWSIM (VII) (Jotani & Baldaniya, 2008 ); TICHAP (VIII) (Jotani & Baldaniya, 2007 ); AWUPAK (IX) (Fun et al., 2011 ); XETKOX (X) (Sridhar et al., 2006 ) and XETKOX01 (XI) (Sridhar et al., 2006).

In the crystal of (I), pairs of weak C—H⋯O hydrogen bonds link molecules related by twofold rotation axes, forming R₂²(10) rings, which in turn are linked by weak C—H⋯N interactions to form chains parallel to [010]. In addition, weak C—H⋯π(arene) interactions link the chains into layers parallel to (001), and π–π interactions connect these layers into a three-dimensional network.

In (II), weak C—H⋯F and C— H⋯O hydrogen bonds connect molecules, forming zigzag chains parallel to [010]. In addition, π–π stacking interactions connect these chains into ladders via inversion-related 4-fluorophenyl groups.

In (III), pairs of weak C—H⋯O hydrogen bonds lead to the formation of inversion dimers. A weak C—H⋯π interaction and π–π stacking interactions are observed.

In (IV), O—H⋯N and C— H⋯S interactions result in (001) layers. The supramolecular assembly is stabilized by π–π stacking interactions between the 2-bromobenzylidene and thiazolopyrimidine rings. In addition, C—H⋯π interactions are also observed.

In (V), co-operative C—H⋯O and C—H⋯π interactions lead to supramolecular chains parallel [100]. These chains are connected via π–π interactions.

The crystal packing of (VI) is influenced by weak intermolecular C—H⋯π interactions and π–π stacking between the thiazole and phenyl rings, which stack the molecules parallel to [001].

In (VII), in addition to intermolecular C— H⋯O hydrogen bonding, short intramolecular C—H⋯S contacts and π–π stacking interactions contribute to the crystal packing.

In (VIII), short intermolecular C—H⋯O, C—H⋯π and π–π stacking interactions contribute to the stability of the crystal packing.

In (IX), molecules are linked into a three-dimensional network by intermolecular C— H⋯O and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by a C—H⋯π interaction.

Compounds (X) and (XI) crystallize in two polymorphic forms having the same space-group type, viz. P1, with Z′ = 2 and Z′ = 1. In both polymorphs, the molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds.

6. Synthesis and crystallization

A mixture of ethyl 4-(4-fluorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2 mmol), 2-(chloromethyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole (2 mmol), potassium iodide (2 mmol) and triethyl amine (2.5 mmol), was refluxed for 4 h in absolute ethanol (20 ml). The reaction mixture was poured onto crushed ice (40 g) and acidified with acetic acid (2 ml). The deposited precipitate was filtered off, washed with cold water, dried and recrystallized from a methanol/DMF mixture.

Yield: 95%; melting point: 493–495 K; IR (KBr) ν_max/cm⁻¹ 3390, 3178, 1693, 1654. ¹H NMR (400 MHz, DMSO-d₆) δ 10.60 (s, 1H, NH), 7.81 (d, J = 8.7 Hz, 2H, Ar—H), 7.44 (t, J = 7.7 Hz, 2H, Ar—H), 7.15 (t, J = 7.7 Hz, 2H, Ar—H), 7.03 (d, J = 8.7 Hz, 2H, Ar—H), 6.13 (s, 1H, C4—H), 4.45 (d, J = 17.4 Hz, 1H, S—CH₂), 4.35 (d, J = 17.3 Hz, 1H, S—CH₂), 4.03 (q, J = 7.1 Hz, 2H, CH₂—CH₃), 3.82 (s, 3H, OCH₃), 2.34 (s, 3H, C6-CH₃), 1.11 (t, J = 7.1 Hz, 3H, CH₂—CH₃). ¹³C NMR (125 MHz, DMSO-d₆) δ 165.59, 163.23, 163.20, 162.65, 153.92, 153.58, 130.57, 130.50, 130.03, 125.90, 115.64, 115.47, 114.05, 105.95, 60.28, 55.87, 54.89, 28.56, 23.06, 14.45. Analysis calculated for C₂₄H₂₃FN₄O₄S (482.53): C 59.74, H 4.80, N 11.61. Found: C 60.02, H 4.89, N 11.87.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms were found in difference-Fourier maps; all C and N-bound H atoms were refined freely. The water molecule was found to be occupationally disordered and was refined with a fixed site occupation factor of 1/4. The H atoms of the water molecules were located in a difference-Fourier map, their bond lengths set to an ideal value of 0.87 Å, and were refined with U_iso(H) = 1.5 U_eq(O) using a riding model.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₄H₂₃FN₄O₄S·0.25H₂O
M_r	487.03
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.4316 (3), 10.8518 (2), 15.5940 (3)
β (°)	109.941 (1)
V (Å³)	2295.74 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.68
Crystal size (mm)	0.15 × 0.14 × 0.11

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.75, 0.84
No. of measured, independent and observed [I > 2σ(I)] reflections	17597, 4576, 4142
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.088, 1.04
No. of reflections	4576
No. of parameters	409
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.56
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2177565

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989022006041/wm5648sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022006041/wm5648Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989022006041/wm5648Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Ethyl (3E)-5-(4-fluorophenyl)3-{[(4-methoxyphenyl)formamido]imino}-7-methyl-2H,3H,5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 0.25-hydrate top

Crystal data top

C₂₄H₂₃FN₄O₄S·0.25H₂O	F(000) = 1018
M_r = 487.03	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.4316 (3) Å	Cell parameters from 9970 reflections
b = 10.8518 (2) Å	θ = 3.3–74.4°
c = 15.5940 (3) Å	µ = 1.68 mm⁻¹
β = 109.941 (1)°	T = 150 K
V = 2295.74 (8) Å³	Block, colourless
Z = 4	0.15 × 0.14 × 0.11 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4576 independent reflections
Radiation source: INCOATEC IµS micro–focus source	4142 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.4°, θ_min = 3.3°
ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→12
T_min = 0.75, T_max = 0.84	l = −19→18
17597 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0389P)² + 1.1637P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4576 reflections	Δρ_max = 0.34 e Å⁻³
409 parameters	Δρ_min = −0.56 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00229 (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.

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. Refinement of the site occupancy factor for the lattice water (O5) converged at ca. 0.25. This was fixed at this value for the remainder of the refinement, the attached hydrogen atoms were located in a difference map and included as riding contributions in idealized positions.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.45709 (2)	0.29846 (3)	0.22568 (2)	0.02637 (11)
F1	0.81951 (11)	0.85095 (10)	0.24433 (11)	0.0709 (4)
O1	0.93592 (8)	0.24379 (11)	0.47803 (8)	0.0365 (3)
O2	0.88439 (7)	0.41670 (10)	0.52684 (7)	0.0294 (2)
O3	0.55706 (8)	0.71812 (10)	0.54550 (7)	0.0307 (2)
O4	0.17420 (9)	1.04606 (11)	0.46165 (8)	0.0390 (3)
N1	0.64445 (8)	0.22708 (11)	0.27415 (8)	0.0220 (2)
N2	0.60560 (8)	0.39869 (10)	0.34918 (8)	0.0200 (2)
N3	0.54560 (8)	0.55654 (10)	0.41266 (8)	0.0206 (2)
N4	0.46512 (8)	0.62737 (11)	0.41154 (8)	0.0209 (2)
H4	0.4182 (14)	0.6419 (17)	0.3587 (13)	0.032 (5)*
C1	0.70873 (9)	0.43284 (13)	0.40035 (10)	0.0213 (3)
H1	0.7122 (12)	0.4512 (15)	0.4634 (11)	0.022 (4)*
C2	0.77324 (10)	0.32264 (13)	0.39918 (10)	0.0224 (3)
C3	0.74171 (10)	0.23233 (13)	0.33574 (10)	0.0224 (3)
C4	0.58287 (10)	0.30597 (12)	0.28731 (9)	0.0207 (3)
C5	0.73684 (9)	0.54708 (13)	0.35807 (10)	0.0233 (3)
C6	0.76870 (10)	0.65331 (14)	0.40974 (11)	0.0291 (3)
H6	0.7696 (14)	0.6545 (17)	0.4744 (13)	0.035 (5)*
C7	0.79756 (12)	0.75620 (15)	0.37183 (14)	0.0365 (4)
H7	0.8223 (15)	0.829 (2)	0.4092 (14)	0.048 (6)*
C8	0.79149 (13)	0.75033 (15)	0.28209 (14)	0.0410 (4)
C9	0.75793 (15)	0.64862 (16)	0.22793 (14)	0.0420 (4)
H9	0.7526 (16)	0.651 (2)	0.1629 (15)	0.050 (6)*
C10	0.73134 (12)	0.54590 (14)	0.26730 (11)	0.0314 (3)
H10	0.7067 (14)	0.4745 (19)	0.2304 (13)	0.038 (5)*
C11	0.87186 (10)	0.32007 (13)	0.46924 (10)	0.0253 (3)
C12	0.97996 (11)	0.42561 (17)	0.59855 (11)	0.0331 (3)
H12A	0.9878 (15)	0.353 (2)	0.6404 (14)	0.045 (5)*
H12B	1.0316 (14)	0.4216 (17)	0.5703 (12)	0.034 (5)*
H12C	0.9642 (16)	0.618 (2)	0.6014 (15)	0.052 (6)*
C13	0.98133 (13)	0.5454 (2)	0.64668 (13)	0.0412 (4)
H13A	1.0491 (17)	0.557 (2)	0.6929 (15)	0.055 (6)*
H13B	0.9329 (18)	0.545 (2)	0.6776 (16)	0.060 (7)*
C14	0.80354 (11)	0.12659 (15)	0.32406 (12)	0.0287 (3)
H14A	0.8649 (17)	0.155 (2)	0.3186 (15)	0.052 (6)*
H14B	0.8240 (16)	0.074 (2)	0.3764 (16)	0.054 (6)*
H14C	0.7663 (16)	0.079 (2)	0.2696 (15)	0.046 (5)*
C15	0.52713 (9)	0.47098 (12)	0.35314 (9)	0.0202 (3)
C16	0.43099 (10)	0.43208 (14)	0.28344 (10)	0.0260 (3)
H16A	0.4032 (14)	0.4974 (19)	0.2389 (13)	0.040 (5)*
H16B	0.3839 (15)	0.4099 (18)	0.3141 (14)	0.043 (5)*
C17	0.48023 (10)	0.71162 (13)	0.48039 (9)	0.0223 (3)
C18	0.39469 (10)	0.79431 (13)	0.47152 (9)	0.0230 (3)
C19	0.41359 (12)	0.90278 (14)	0.52329 (10)	0.0289 (3)
H19	0.4793 (15)	0.9188 (17)	0.5629 (13)	0.036 (5)*
C20	0.33869 (12)	0.98472 (15)	0.51747 (11)	0.0331 (3)
H20	0.3508 (16)	1.062 (2)	0.5510 (15)	0.053 (6)*
C21	0.24267 (11)	0.95909 (15)	0.46124 (10)	0.0294 (3)
C22	0.22193 (11)	0.85134 (15)	0.40997 (10)	0.0287 (3)
H22	0.1533 (15)	0.8314 (18)	0.3709 (13)	0.037 (5)*
C23	0.29829 (11)	0.76979 (14)	0.41584 (10)	0.0260 (3)
H23	0.2829 (13)	0.6946 (17)	0.3814 (12)	0.031 (5)*
C24	0.07367 (14)	1.0253 (2)	0.40748 (14)	0.0456 (5)
H24A	0.0502 (16)	0.946 (2)	0.4247 (15)	0.054 (6)*
H24B	0.0650 (16)	1.025 (2)	0.3411 (16)	0.053 (6)*
H24C	0.0390 (16)	1.093 (2)	0.4203 (14)	0.048 (6)*
O5	0.7191 (3)	0.9508 (5)	0.0994 (3)	0.0378 (10)	0.25
H5A	0.766259	0.901704	0.130626	0.057*	0.25
H5B	0.667996	0.902764	0.079072	0.057*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01757 (17)	0.0260 (2)	0.0312 (2)	0.00125 (12)	0.00266 (13)	−0.00720 (13)
F1	0.1061 (11)	0.0263 (6)	0.1191 (11)	−0.0171 (6)	0.0888 (10)	−0.0055 (6)
O1	0.0214 (5)	0.0345 (6)	0.0476 (7)	0.0093 (4)	0.0038 (5)	−0.0055 (5)
O2	0.0177 (5)	0.0313 (6)	0.0326 (6)	0.0026 (4)	0.0002 (4)	−0.0057 (4)
O3	0.0271 (5)	0.0336 (6)	0.0274 (5)	0.0038 (4)	0.0040 (4)	−0.0039 (4)
O4	0.0370 (6)	0.0405 (7)	0.0400 (6)	0.0175 (5)	0.0137 (5)	−0.0051 (5)
N1	0.0198 (5)	0.0194 (6)	0.0257 (6)	0.0010 (4)	0.0064 (5)	−0.0013 (4)
N2	0.0151 (5)	0.0186 (6)	0.0246 (6)	0.0011 (4)	0.0046 (4)	−0.0013 (4)
N3	0.0174 (5)	0.0202 (6)	0.0246 (6)	0.0028 (4)	0.0078 (4)	0.0011 (4)
N4	0.0179 (5)	0.0216 (6)	0.0231 (6)	0.0044 (4)	0.0069 (5)	0.0005 (4)
C1	0.0151 (6)	0.0211 (7)	0.0256 (7)	0.0001 (5)	0.0042 (5)	−0.0028 (5)
C2	0.0169 (6)	0.0208 (7)	0.0284 (7)	0.0019 (5)	0.0062 (5)	0.0005 (5)
C3	0.0190 (6)	0.0205 (7)	0.0276 (7)	0.0016 (5)	0.0079 (5)	0.0023 (5)
C4	0.0206 (6)	0.0181 (7)	0.0230 (7)	−0.0001 (5)	0.0067 (5)	0.0005 (5)
C5	0.0146 (6)	0.0199 (7)	0.0348 (8)	0.0012 (5)	0.0077 (5)	−0.0021 (5)
C6	0.0207 (7)	0.0237 (8)	0.0399 (9)	0.0007 (5)	0.0066 (6)	−0.0057 (6)
C7	0.0270 (8)	0.0204 (8)	0.0640 (11)	−0.0040 (6)	0.0179 (8)	−0.0093 (7)
C8	0.0439 (9)	0.0204 (8)	0.0744 (13)	−0.0032 (7)	0.0406 (9)	0.0001 (8)
C9	0.0582 (11)	0.0270 (9)	0.0568 (11)	−0.0018 (7)	0.0402 (10)	−0.0014 (7)
C10	0.0373 (8)	0.0227 (8)	0.0403 (9)	−0.0035 (6)	0.0212 (7)	−0.0051 (6)
C11	0.0191 (6)	0.0238 (7)	0.0312 (7)	0.0015 (5)	0.0064 (6)	−0.0005 (6)
C12	0.0177 (7)	0.0431 (10)	0.0315 (8)	0.0004 (6)	−0.0005 (6)	−0.0031 (7)
C13	0.0284 (8)	0.0560 (12)	0.0348 (9)	−0.0025 (8)	0.0053 (7)	−0.0140 (8)
C14	0.0239 (7)	0.0252 (8)	0.0356 (8)	0.0050 (6)	0.0083 (6)	−0.0037 (6)
C15	0.0171 (6)	0.0186 (7)	0.0246 (7)	0.0011 (5)	0.0068 (5)	0.0028 (5)
C16	0.0187 (6)	0.0254 (8)	0.0303 (8)	0.0020 (5)	0.0038 (6)	−0.0048 (6)
C17	0.0226 (7)	0.0217 (7)	0.0234 (7)	0.0007 (5)	0.0090 (5)	0.0015 (5)
C18	0.0246 (7)	0.0235 (7)	0.0234 (7)	0.0023 (5)	0.0113 (6)	0.0002 (5)
C19	0.0287 (8)	0.0288 (8)	0.0292 (8)	0.0003 (6)	0.0098 (6)	−0.0039 (6)
C20	0.0378 (9)	0.0286 (8)	0.0336 (8)	0.0043 (6)	0.0134 (7)	−0.0072 (6)
C21	0.0322 (8)	0.0313 (8)	0.0286 (8)	0.0110 (6)	0.0155 (6)	0.0018 (6)
C22	0.0254 (7)	0.0341 (8)	0.0283 (7)	0.0042 (6)	0.0114 (6)	−0.0016 (6)
C23	0.0256 (7)	0.0274 (8)	0.0273 (7)	0.0014 (6)	0.0121 (6)	−0.0035 (6)
C24	0.0357 (9)	0.0540 (12)	0.0455 (11)	0.0212 (9)	0.0119 (8)	−0.0026 (9)
O5	0.027 (2)	0.042 (3)	0.039 (3)	−0.0069 (19)	0.0036 (19)	0.006 (2)

Geometric parameters (Å, º) top

S1—C4	1.7422 (14)	C9—C10	1.388 (2)
S1—C16	1.8130 (15)	C9—H9	0.99 (2)
F1—C8	1.3657 (19)	C10—H10	0.96 (2)
O1—C11	1.2133 (18)	C12—C13	1.498 (2)
O2—C11	1.3522 (18)	C12—H12A	1.00 (2)
O2—C12	1.4526 (17)	C12—H12B	0.988 (19)
O3—C17	1.2236 (17)	C13—H12C	1.03 (2)
O4—C21	1.3680 (18)	C13—H13A	1.00 (2)
O4—C24	1.426 (2)	C13—H13B	0.98 (3)
N1—C4	1.2996 (18)	C14—H14A	0.97 (2)
N1—C3	1.4058 (17)	C14—H14B	0.96 (2)
N2—C4	1.3546 (17)	C14—H14C	0.98 (2)
N2—C15	1.3963 (17)	C15—C16	1.5020 (19)
N2—C1	1.4762 (16)	C16—H16A	0.98 (2)
N3—C15	1.2750 (18)	C16—H16B	0.98 (2)
N3—N4	1.3880 (15)	C17—C18	1.4939 (19)
N4—C17	1.3698 (18)	C18—C23	1.391 (2)
N4—H4	0.885 (19)	C18—C19	1.401 (2)
C1—C2	1.5194 (18)	C19—C20	1.379 (2)
C1—C5	1.5226 (19)	C19—H19	0.96 (2)
C1—H1	0.987 (17)	C20—C21	1.392 (2)
C2—C3	1.356 (2)	C20—H20	0.97 (2)
C2—C11	1.4694 (19)	C21—C22	1.390 (2)
C3—C14	1.5024 (19)	C22—C23	1.392 (2)
C5—C10	1.391 (2)	C22—H22	0.99 (2)
C5—C6	1.392 (2)	C23—H23	0.960 (19)
C6—C7	1.392 (2)	C24—H24A	0.99 (2)
C6—H6	1.004 (19)	C24—H24B	1.00 (2)
C7—C8	1.373 (3)	C24—H24C	0.95 (2)
C7—H7	0.97 (2)	O5—H5A	0.8700
C8—C9	1.374 (3)	O5—H5B	0.8701

C4—S1—C16	92.44 (6)	C13—C12—H12B	112.3 (11)
C11—O2—C12	116.09 (11)	H12A—C12—H12B	108.7 (16)
C21—O4—C24	118.60 (14)	C12—C13—H12C	111.3 (12)
C4—N1—C3	116.27 (12)	C12—C13—H13A	107.9 (13)
C4—N2—C15	116.48 (11)	H12C—C13—H13A	110.2 (18)
C4—N2—C1	121.74 (11)	C12—C13—H13B	110.9 (14)
C15—N2—C1	121.23 (11)	H12C—C13—H13B	107.1 (18)
C15—N3—N4	115.33 (11)	H13A—C13—H13B	109.4 (19)
C17—N4—N3	116.80 (11)	C3—C14—H14A	111.4 (13)
C17—N4—H4	118.6 (12)	C3—C14—H14B	112.1 (14)
N3—N4—H4	118.8 (12)	H14A—C14—H14B	103.9 (18)
N2—C1—C2	107.75 (11)	C3—C14—H14C	109.4 (12)
N2—C1—C5	109.80 (11)	H14A—C14—H14C	109.8 (18)
C2—C1—C5	112.38 (11)	H14B—C14—H14C	110.1 (18)
N2—C1—H1	106.8 (9)	N3—C15—N2	118.03 (12)
C2—C1—H1	110.3 (9)	N3—C15—C16	130.06 (12)
C5—C1—H1	109.6 (10)	N2—C15—C16	111.90 (11)
C3—C2—C11	121.84 (12)	C15—C16—S1	106.69 (9)
C3—C2—C1	121.53 (12)	C15—C16—H16A	111.4 (12)
C11—C2—C1	116.62 (12)	S1—C16—H16A	109.4 (11)
C2—C3—N1	122.42 (12)	C15—C16—H16B	109.7 (12)
C2—C3—C14	125.10 (13)	S1—C16—H16B	109.9 (12)
N1—C3—C14	112.47 (12)	H16A—C16—H16B	109.8 (16)
N1—C4—N2	126.10 (12)	O3—C17—N4	123.09 (13)
N1—C4—S1	121.47 (10)	O3—C17—C18	121.90 (13)
N2—C4—S1	112.41 (10)	N4—C17—C18	115.00 (12)
C10—C5—C6	119.33 (14)	C23—C18—C19	118.49 (13)
C10—C5—C1	120.14 (13)	C23—C18—C17	124.17 (13)
C6—C5—C1	120.53 (13)	C19—C18—C17	117.34 (13)
C5—C6—C7	120.41 (16)	C20—C19—C18	120.67 (15)
C5—C6—H6	118.7 (11)	C20—C19—H19	120.6 (11)
C7—C6—H6	120.9 (11)	C18—C19—H19	118.8 (11)
C8—C7—C6	118.11 (15)	C19—C20—C21	120.16 (15)
C8—C7—H7	122.1 (12)	C19—C20—H20	121.9 (13)
C6—C7—H7	119.8 (12)	C21—C20—H20	117.9 (13)
F1—C8—C7	118.48 (16)	O4—C21—C22	124.66 (14)
F1—C8—C9	118.13 (17)	O4—C21—C20	115.13 (14)
C7—C8—C9	123.39 (16)	C22—C21—C20	120.20 (14)
C8—C9—C10	117.76 (17)	C21—C22—C23	119.12 (14)
C8—C9—H9	119.7 (13)	C21—C22—H22	120.7 (11)
C10—C9—H9	122.5 (13)	C23—C22—H22	120.2 (11)
C9—C10—C5	120.96 (15)	C18—C23—C22	121.34 (14)
C9—C10—H10	119.1 (12)	C18—C23—H23	120.2 (11)
C5—C10—H10	119.9 (12)	C22—C23—H23	118.4 (11)
O1—C11—O2	122.00 (13)	O4—C24—H24A	110.4 (13)
O1—C11—C2	127.18 (14)	O4—C24—H24B	110.9 (13)
O2—C11—C2	110.81 (11)	H24A—C24—H24B	110.1 (18)
O2—C12—C13	106.88 (13)	O4—C24—H24C	104.9 (13)
O2—C12—H12A	108.3 (12)	H24A—C24—H24C	111.1 (18)
C13—C12—H12A	112.1 (12)	H24B—C24—H24C	109.4 (18)
O2—C12—H12B	108.5 (11)	H5A—O5—H5B	104.0

C15—N3—N4—C17	173.45 (12)	C1—C5—C10—C9	−179.13 (15)
C4—N2—C1—C2	−21.62 (17)	C12—O2—C11—O1	1.5 (2)
C15—N2—C1—C2	167.22 (11)	C12—O2—C11—C2	−179.00 (12)
C4—N2—C1—C5	101.08 (14)	C3—C2—C11—O1	2.3 (2)
C15—N2—C1—C5	−70.08 (15)	C1—C2—C11—O1	−176.78 (15)
N2—C1—C2—C3	20.41 (18)	C3—C2—C11—O2	−177.21 (13)
C5—C1—C2—C3	−100.69 (15)	C1—C2—C11—O2	3.75 (18)
N2—C1—C2—C11	−160.54 (12)	C11—O2—C12—C13	173.66 (14)
C5—C1—C2—C11	78.36 (15)	N4—N3—C15—N2	178.26 (11)
C11—C2—C3—N1	173.50 (13)	N4—N3—C15—C16	−2.1 (2)
C1—C2—C3—N1	−7.5 (2)	C4—N2—C15—N3	177.79 (12)
C11—C2—C3—C14	−5.0 (2)	C1—N2—C15—N3	−10.60 (19)
C1—C2—C3—C14	174.03 (14)	C4—N2—C15—C16	−1.93 (17)
C4—N1—C3—C2	−7.2 (2)	C1—N2—C15—C16	169.67 (12)
C4—N1—C3—C14	171.48 (13)	N3—C15—C16—S1	−176.70 (12)
C3—N1—C4—N2	6.2 (2)	N2—C15—C16—S1	2.98 (14)
C3—N1—C4—S1	−171.99 (10)	C4—S1—C16—C15	−2.61 (11)
C15—N2—C4—N1	−178.53 (13)	N3—N4—C17—O3	−7.08 (19)
C1—N2—C4—N1	9.9 (2)	N3—N4—C17—C18	174.20 (11)
C15—N2—C4—S1	−0.18 (15)	O3—C17—C18—C23	−160.50 (14)
C1—N2—C4—S1	−171.74 (10)	N4—C17—C18—C23	18.2 (2)
C16—S1—C4—N1	−179.84 (12)	O3—C17—C18—C19	19.1 (2)
C16—S1—C4—N2	1.73 (11)	N4—C17—C18—C19	−162.14 (13)
N2—C1—C5—C10	−58.95 (16)	C23—C18—C19—C20	−1.5 (2)
C2—C1—C5—C10	60.97 (17)	C17—C18—C19—C20	178.83 (14)
N2—C1—C5—C6	121.37 (13)	C18—C19—C20—C21	1.3 (2)
C2—C1—C5—C6	−118.72 (14)	C24—O4—C21—C22	1.3 (2)
C10—C5—C6—C7	−1.9 (2)	C24—O4—C21—C20	−178.54 (16)
C1—C5—C6—C7	177.79 (13)	C19—C20—C21—O4	179.23 (14)
C5—C6—C7—C8	1.4 (2)	C19—C20—C21—C22	−0.6 (2)
C6—C7—C8—F1	179.90 (15)	O4—C21—C22—C23	−179.73 (14)
C6—C7—C8—C9	0.4 (3)	C20—C21—C22—C23	0.1 (2)
F1—C8—C9—C10	178.81 (16)	C19—C18—C23—C22	1.0 (2)
C7—C8—C9—C10	−1.7 (3)	C17—C18—C23—C22	−179.37 (13)
C8—C9—C10—C5	1.2 (3)	C21—C22—C23—C18	−0.3 (2)
C6—C5—C10—C9	0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.885 (19)	2.164 (19)	2.9888 (17)	154.8 (16)
C1—H1···O5ⁱⁱ	0.987 (17)	2.345 (18)	3.307 (5)	164.7 (13)
C7—H7···O4ⁱⁱⁱ	0.97 (2)	2.41 (2)	3.285 (2)	148.7 (17)
C13—H13B···F1ⁱⁱ	0.98 (3)	2.49 (3)	3.386 (2)	153.0 (19)
C16—H16A···N1ⁱ	0.98 (2)	2.58 (2)	3.4019 (19)	142.4 (15)
C16—H16B···O5^iv	0.98 (2)	2.37 (2)	3.282 (5)	154.6 (16)
C24—H24A···O1^v	0.99 (2)	2.53 (2)	3.450 (3)	154.6 (18)
C24—H24C···O1^vi	0.95 (2)	2.57 (2)	3.504 (2)	167.8 (17)
O5—H5A···F1	0.87	1.76	2.479 (5)	138
O5—H5B···O3^vii	0.87	2.00	2.863 (5)	174

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) −x+1, −y+1, −z+1; (vi) x−1, y+1, z; (vii) x, −y+3/2, z−1/2.

Summary of short interatomic contacts (Å) in the title compound. top

Asterisks relate to atoms of the underoccupied water molecule.

Contact	Distance	Symmetry operation
N1···H4	2.165	1 - x, -1/2 + y, 1/2 - z
F1···H13B	2.49	x, 3/2 - y, -1/2 + z
F1···*H5A	1.76	x, y, z
F1···H14C	2.66	x, 1 + y, z
H14A···H24C	2.56	1 + x, -1 + y, z
H12C···O1	2.66	2 - x, 1 - y, 1 - z
H16B···O3	2.49	1 - x, 1 - y, 1 - z
O3···*H5B	2.00	x, 3/2 - y, 1/2 + z
H7···O4	2.41	1 - x, 2 - y, 1 - z
H16B···*H5B	2.05	1 - x, -1/2 + y, 1/2 - z
H13A···H24B	2.41	1 + x, 3/2 - y, 1/2 + z
H14C···*O5	2.87	x, -1 + y, z

Acknowledgements

Author contributions are as follows: synthesis and organic chemistry parts preparation, AMA, FAFR, SKM; conceptualization and study guide, AMA, SKM; financial support, MAA MAU?; crystal data production and validation, JTM; paper preparation and Hirshfeld study, MA, SKM.

Funding information

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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