Crystal structure and Hirshfeld surface analysis of (2Z)-3-oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methylidene]butanamide monohydrate

Safarova, A.S.; Khalilov, A.N.; Akkurt, M.; Brito, I.; Bhattarai, A.; Naghiyev, F.N.; Mamedov, I.G.

doi:10.1107/S2056989023009799

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ISSN: 2056-9890

Volume 79| Part 12| December 2023| Pages 1142-1146

https://doi.org/10.1107/S2056989023009799

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Crystal structure and Hirshfeld surface analysis of (2Z)-3-oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methylidene]butanamide monohydrate

Ayten S. Safarova,^a Ali N. Khalilov,^b,^a Mehmet Akkurt,^c Ivan Brito,^d Ajaya Bhattarai,^e ^* Farid N. Naghiyev ^a and Ibrahim G. Mamedov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, AZ1148 Baku, Azerbaijan, ^b"Composite Materials' Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, AZ1063, Baku, Azerbaijan, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^dDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Angamos 601, Casilla 170, Antofagasta 1240000, Chile, and ^eDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 31 October 2023; accepted 9 November 2023; online 14 November 2023)

In the title compound, C₁₅H₁₄N₂O₂·H₂O, the 1H-pyrrole ring makes a dihedral angle of 59.95 (13)° with the phenyl ring. In the crystal, the molecules are connected by C—H⋯O hydrogen bonds into layers parallel to the (020) plane, while two molecules are connected to the water molecule by two N—H⋯O hydrogen bonds and one molecule by an O—H⋯O hydrogen bond. C—H⋯π and π–π interactions further link the molecules into chains extending in the [ $[\overline{1}]$ 01] direction and stabilize the molecular packing. According to a Hirshfeld surface study, H⋯H (49.4%), C⋯H/H⋯C (23.2%) and O⋯H/H⋯O (20.0%) interactions are the most significant contributors to the crystal packing.

Keywords: crystal structure; 1H-pyrrole ring; hydrogen bonds; Hirshfeld surface analysis.

CCDC reference: 2306713

1. Chemical context

Heterocyclic and carbocyclic aromatic systems are the most important compounds in organic chemistry (Gurbanov et al., 2017 ; Aliyeva et al., 2023 ). Organic synthesis is developing enormously with newer aromatic compounds having been obtained for diverse medicinal and commercial purposes (Maharramov et al., 2021 ; Poustforoosh et al., 2022 ; Gurbanov et al., 2022a ,b ). Nowadays, the application of five and six-membered heterocycles in particular has been expanded in different branches of chemistry, including coordination chemistry (Gurbanov et al., 2021 ; Mahmoudi et al., 2021 ), drug design and development (Çelik et al., 2023 ) and material science (Velásquez et al., 2019 ; Afkhami et al., 2019 ). The pyrrole core is the most common five-membered heteroaromatic ring system in nitrogen heterocycles (Mahmoudi et al., 2017 ). It is an essential structural motif present in many natural tetrapyrrole scaffolds of heme and related cofactors (chlorophyll a, heme b, vitamin B₁₂, factor 430) and other bioactive molecules such as porphobilinogen, nargenicin and prodigiosin (Walsh et al., 2006 ). The combination of different pharmacophores in a pyrrole ring system has led to the formation of more active compounds, such as elopiprazole, lorpiprazole, isamoltane, obatoclax (Bhardwaj et al., 2015 ). On the other hand, there have been a variety of significant examples of pyrrole derivatives used as target products as well as synthetic intermediates (Naghiyev et al., 2020 , 2021 , 2022 ).

2. Structural commentary

The title compound crystallizes with one water molecule in the asymmetric unit (Fig. 1). The 1H-pyrrole ring (N2/C10–C13) makes a dihedral angle of 59.95 (13)° with the phenyl ring (C1–C6). The conformation is stabilized by an intramolecular C5—H5⋯O1 interaction (Table 1). In addition, an OW1—HW1⋯O1 hydrogen bond is observed between the main molecule and the water molecule in the asymmetric unit (Table 1). The 1H-pyrrole ring and N-phenylformamide substituents on the C8=C9 double bond are in a cis configuration [the C7—C8—C9—C10 torsion angle is 1.5 (3) °] and the 1H-pyrrole ring and the acetaldehyde substituents are in a trans configuration [the C14—C8—C9—C10 torsion angle is 179.17 (18) °].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2/C10–C13 pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.41	2.906 (3)	113
C13—H13⋯O1ⁱ	0.93	2.56	3.480 (3)	173
N1—HN1⋯OW1ⁱⁱ	0.91 (2)	1.99 (2)	2.898 (2)	179 (2)
N2—HN2⋯OW1ⁱⁱⁱ	0.89 (2)	2.02 (2)	2.901 (2)	173 (2)
OW1—HW1⋯O1	0.92 (3)	1.80 (3)	2.718 (2)	177 (2)
OW1—HW2⋯O2^iv	0.87 (3)	1.92 (3)	2.750 (2)	160 (2)
C15—H15C⋯Cg1ⁱⁱⁱ	0.96	2.66	3.536 (3)	151
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 30% probability level.

The other torsion angles C5—C6—N1—C7, C6—N1—C7—O1, C6—N1—C7—C8, N1—C7—C8—C14, N1—C7—C8—C9, C7—C8—C14—C15 and C8—C9—C10—C11 are −30.7 (3), 6.7 (3), −172.19 (17), 85.2 (2), −97.0 (2), −176.03 (18) and −1.0 (4)°, respectively. The geometric parameters of the title compound are normal and comparable to that of related compound listed in the Database survey section.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, the molecules are also connected by C—H⋯O hydrogen bonds in layers parallel to the (020) plane, while two molecules are connected to the water molecule by two N—H⋯O hydrogen bonds and one molecule by an O—H⋯O hydrogen bond (Table 1, Figs. 2 and 3). C—H⋯π and π–π interactions [Cg2⋯Cg2(1 − x, 1 − y, 1 − z) = 3.8404 (16) Å, slippage = 0.858 Å; Cg2 is the centroid of phenyl ring C1–C6] link the molecules into chains extending in the [ $[\overline{1}]$ 01] direction and stabilize the molecular packing (Table 1, Figs. 4 and 5).

Figure 2
View of the crystal packing of the title compound along the a-axis showing N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds as dashed lines.

Figure 3
View of the crystal packing of the title compound along the b-axis showing N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds as dashed lines.

Figure 4
View of the crystal packing of the title compound along the a-axis showing the C—H⋯π and π–π interactions as dashed lines.

Figure 5
View of the crystal packing of the title compound along the c-axis showing the C—H⋯π and π–π interactions as dashed lines.

Crystal Explorer 17.5 (Spackman et al., 2021 ) was used to generate Hirshfeld surfaces and two-dimensional fingerprint plots in order to quantify the intermolecular interactions in the crystal. The Hirshfeld surfaces were mapped over d_norm in the range −0.6778 (red) to +1.5015 (blue) a.u. (Fig. 6). The interactions given in Table 2 play a key role in the molecular packing of the title compound. The most important interatomic contact is H⋯H as it makes the highest contribution to the crystal packing (49.4%, Fig. 7b). Other major contributors are C⋯H/H⋯C (23.2%, Fig. 7c) and O⋯H/H⋯O (20.0%, Fig. 7d) interactions. Other smaller contributions are made by C⋯C (3.4%), N⋯H/H⋯N (3.3%), C⋯N/N⋯C (0.4%) and C⋯O/O⋯C (0.3%) interactions.

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

Contact	Distance	Symmetry operation
O1⋯HW1	1.80	x, y, z
O1⋯H13	2.56	x, 1 + y, z
O2⋯HW2	1.92	$[{3\over 2}]$ − x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z
HN1⋯OW1	1.99	− $[{1\over 2}]$ + x, 1 − y, z
N2⋯H15B	2.92	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
HN2⋯OW1	2.02	$[{3\over 2}]$ − x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z
H15C⋯N2	2.76	$[{3\over 2}]$ − x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z
H5⋯H5	2.36	$[{3\over 2}]$ − x, y, 1 − z
H3⋯C11	3.06	1 − x, 1 − y, 1 − z
H3⋯H15A	2.59	x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z

Figure 6
(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 −0.6778 to +1.5015 a.u.

Figure 7
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O interactions. [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.43, last update November 2022; Groom et al., 2016 ) for structures containing the fragment N—C—CH=C—C(=O)—NH, in which the N—C bond is part of a five-membered ring and the CH=C bond is acyclic, resulted in one hit, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-[(2Z)-3-(pyrrolidin-2-yl)-2-methyl-2-propenoyl]-L-alanine methylamide dichloromethane solvate hydrate (CSD refcode SEFCUC; Grison et al., 2005 ).

In the crystal of SEFCUC, molecules are connected by N—H⋯O and C—H⋯O hydrogen bonds, forming molecular layers parallel to the (001) plane. These layers are connected to each other by van der Waals forces. Torsion angles at the central C—C=C—C(=O)—NH unit in SEFCUC, i.e. the torsion angles C9—C13—C14—C16 and C13—C14—C16—N3 are −3.1 (5) and −53.1 (4)°, respectively. SEFCUC shows a folded conformation due to an intramolecular N—H⋯O hydrogen bond. The amide group is trans-planar, as in the title compound.

5. Synthesis and crystallization

To a solution of pyrrole-2-carboxaldehyde (1 g, 10 mmol) and acetoacetanilide (1.77 g, 10 mmol) in ethanol (80%, 20 mL), were added methylpiperazine (3–4 drops) and the mixture was stirred at room temperature for 2 h. The reaction mixture was then left overnight. The precipitated crystals were separated by filtration and recrystallized from an ethanol/water (1:1) solution (yield 69%; m.p. 513–514 K).

¹H NMR (300 MHz, DMSO-d₆, δ): 2.34 (s, 3H, CH₃), 6.21 (d, 1H, CH_pyr.), 6.57 (1H, d, CH_pyr.), 7.10 (t, 1H, CH_pyr), 7.14 (t, 1H, CH_arom.), 7.35 (m, 2H; 2CH_arom.), 7.57 (s, 1H, CH=), 7.70 (d, 2H, 2CH_arom.), 10.41 (s, 1H, NH), 11.52 (s, 1H, NH). ¹³C NMR (75 MHz, DMSO-d₆ δ): 26.45 (CH₃), 112.12 (CH_pyr.), 114.66 (CH_pyr.), 119.74 (2CH_arom.), 124.08 (CH_pyr.), 126.70 (CH_arom.), 129.37 (2CH_arom.), 130.66 (C_pyr.), 136.83 (CH=), 139.58 (C_quat.), 139.70 (C_quat.), 166.74 (C=O), 195.29 (C=O).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen atoms of the water molecule and the hydrogen atoms bound to nitrogen were located in difference-Fourier maps and refined with fixed positional thermal displacement parameters and with U_iso(H) = 1.2U_eq(N) or 1.5U_eq(O). All carbon-bound hydrogen atoms were positioned geometrically (C—H = 0.93–0.96 Å) and were included in the refinement in the riding-model approximation with U_iso(H) = 1.2 or 1.5U_eq(C). One reflection (0 1 1), affected by the beam stop, was omitted in the final cycles of refinement. Owing to poor agreement between observed and calculated intensities, fourteen outliers ( $[\overline{15}]$ 1 10, $[\overline{2}]$ 3 15, 8 4 16, 16 0 0, $[\overline{7}]$ 3 18, 0 5 23, 2 3 7, $[\overline{1}]$ 2 21, $[\overline{7}]$ 7 18, $[\overline{6}]$ 6 8, 1 5 18, $[\overline{1}]$ 3 18, 0 2 14, 5 5 20) were omitted during the final refinement cycle. The value of R(int) should normally be considerably lower than 0.10. The value of R(int) of 0.205 in this study may be high due to poor crystal quality.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂·H₂O
M_r	272.30
Crystal system, space group	Monoclinic, I2/a
Temperature (K)	294
a, b, c (Å)	13.7420 (13), 8.8912 (13), 23.114 (2)
β (°)	94.742 (4)
V (Å³)	2814.5 (6)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.29 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	98978, 2677, 1729
R_int	0.205
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.05
No. of reflections	2677
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18
Computer programs: APEX2 and SAINT (Bruker, 2018 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2306713

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023009799/vm2291sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023009799/vm2291Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023009799/vm2291Isup3.cml

checkCIF report

Computing details top

(2Z)-3-Oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methylidene]butanamide monohydrate top

Crystal data top

C₁₅H₁₄N₂O₂·H₂O	F(000) = 1152
M_r = 272.30	D_x = 1.285 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 13.7420 (13) Å	Cell parameters from 7717 reflections
b = 8.8912 (13) Å	θ = 3.2–21.8°
c = 23.114 (2) Å	µ = 0.09 mm⁻¹
β = 94.742 (4)°	T = 294 K
V = 2814.5 (6) Å³	Prism, colourless
Z = 8	0.29 × 0.24 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.205
φ and ω scans	θ_max = 25.7°, θ_min = 2.7°
98978 measured reflections	h = −16→16
2677 independent reflections	k = −10→10
1729 reflections with I > 2σ(I)	l = −28→28

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0357P)² + 2.2064P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2677 reflections	Δρ_max = 0.14 e Å⁻³
194 parameters	Δρ_min = −0.18 e Å⁻³

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
C1	0.45829 (16)	0.6822 (3)	0.43032 (9)	0.0540 (6)
H1	0.408073	0.670947	0.401110	0.065*
C2	0.4445 (2)	0.7687 (3)	0.47832 (10)	0.0710 (7)
H2	0.384992	0.816610	0.481260	0.085*
C3	0.5178 (2)	0.7850 (3)	0.52188 (11)	0.0699 (7)
H3	0.508515	0.845175	0.553880	0.084*
C4	0.60437 (19)	0.7124 (3)	0.51790 (10)	0.0669 (7)
H4	0.653634	0.721325	0.547795	0.080*
C5	0.61958 (16)	0.6259 (3)	0.47001 (9)	0.0532 (6)
H5	0.678910	0.576957	0.467656	0.064*
C6	0.54696 (14)	0.6122 (2)	0.42572 (8)	0.0388 (5)
C7	0.64024 (14)	0.5036 (2)	0.34901 (8)	0.0372 (4)
C8	0.62601 (13)	0.4259 (2)	0.29110 (8)	0.0361 (4)
C9	0.63778 (13)	0.2768 (2)	0.28452 (8)	0.0398 (5)
H9	0.628673	0.241390	0.246603	0.048*
C10	0.66233 (14)	0.1657 (2)	0.32780 (8)	0.0415 (5)
C11	0.68283 (17)	0.1689 (3)	0.38755 (9)	0.0547 (6)
H11	0.686480	0.254312	0.410856	0.066*
C12	0.69700 (18)	0.0209 (3)	0.40637 (10)	0.0614 (6)
H12	0.711383	−0.010172	0.444544	0.074*
C13	0.68602 (17)	−0.0701 (3)	0.35893 (10)	0.0571 (6)
H13	0.691324	−0.174348	0.359127	0.069*
C14	0.60180 (14)	0.5269 (2)	0.24196 (8)	0.0445 (5)
C15	0.57908 (17)	0.4655 (3)	0.18195 (9)	0.0588 (6)
H15A	0.556811	0.545433	0.156270	0.088*
H15B	0.529029	0.390312	0.182627	0.088*
H15C	0.636866	0.421282	0.168541	0.088*
N1	0.55800 (12)	0.52714 (18)	0.37468 (7)	0.0397 (4)
HN1	0.5032 (16)	0.497 (2)	0.3534 (9)	0.048*
N2	0.66617 (13)	0.01667 (19)	0.31163 (8)	0.0472 (4)
HN2	0.6547 (16)	−0.017 (2)	0.2755 (10)	0.057*
O1	0.72199 (10)	0.54315 (16)	0.36963 (6)	0.0486 (4)
O2	0.60026 (13)	0.66292 (18)	0.25062 (6)	0.0653 (5)
OW1	0.88137 (11)	0.57116 (18)	0.30826 (6)	0.0496 (4)
HW1	0.8260 (19)	0.564 (3)	0.3282 (10)	0.074*
HW2	0.8891 (18)	0.664 (3)	0.2981 (11)	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0510 (13)	0.0643 (14)	0.0468 (12)	0.0125 (11)	0.0048 (10)	−0.0042 (11)
C2	0.0739 (17)	0.0797 (18)	0.0607 (16)	0.0279 (14)	0.0127 (13)	−0.0136 (14)
C3	0.0875 (19)	0.0703 (17)	0.0534 (14)	0.0020 (14)	0.0149 (13)	−0.0227 (13)
C4	0.0690 (16)	0.0836 (19)	0.0474 (13)	−0.0054 (14)	0.0004 (11)	−0.0176 (13)
C5	0.0487 (12)	0.0657 (15)	0.0445 (12)	0.0039 (11)	0.0004 (10)	−0.0096 (11)
C6	0.0448 (11)	0.0374 (11)	0.0347 (10)	−0.0020 (9)	0.0056 (8)	−0.0001 (8)
C7	0.0404 (11)	0.0299 (10)	0.0414 (11)	0.0011 (8)	0.0053 (8)	0.0011 (8)
C8	0.0360 (10)	0.0380 (11)	0.0348 (10)	−0.0003 (8)	0.0054 (8)	−0.0022 (8)
C9	0.0381 (10)	0.0442 (12)	0.0376 (11)	−0.0006 (9)	0.0058 (8)	−0.0054 (9)
C10	0.0440 (11)	0.0355 (11)	0.0460 (12)	0.0030 (9)	0.0086 (9)	−0.0039 (9)
C11	0.0725 (15)	0.0457 (13)	0.0462 (13)	0.0066 (11)	0.0074 (11)	−0.0015 (10)
C12	0.0794 (17)	0.0542 (15)	0.0508 (13)	0.0089 (12)	0.0066 (12)	0.0085 (12)
C13	0.0652 (15)	0.0375 (12)	0.0696 (16)	0.0041 (11)	0.0108 (12)	0.0073 (12)
C14	0.0416 (11)	0.0487 (14)	0.0439 (12)	0.0040 (9)	0.0071 (9)	0.0034 (10)
C15	0.0593 (14)	0.0750 (16)	0.0414 (12)	0.0077 (12)	0.0007 (10)	0.0015 (11)
N1	0.0361 (9)	0.0454 (10)	0.0376 (9)	−0.0012 (7)	0.0030 (7)	−0.0074 (8)
N2	0.0526 (10)	0.0371 (10)	0.0526 (11)	0.0007 (8)	0.0076 (8)	−0.0068 (9)
O1	0.0381 (8)	0.0556 (9)	0.0523 (8)	−0.0057 (7)	0.0049 (6)	−0.0094 (7)
O2	0.0966 (13)	0.0433 (10)	0.0563 (10)	0.0071 (8)	0.0070 (8)	0.0089 (8)
OW1	0.0450 (8)	0.0511 (9)	0.0533 (9)	0.0040 (7)	0.0078 (7)	0.0091 (7)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C9—H9	0.9300
C1—C6	1.380 (3)	C10—N2	1.379 (3)
C1—H1	0.9300	C10—C11	1.387 (3)
C2—C3	1.371 (4)	C11—C12	1.395 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.363 (4)	C12—C13	1.361 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (3)	C13—N2	1.347 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.375 (3)	C14—O2	1.226 (2)
C5—H5	0.9300	C14—C15	1.500 (3)
C6—N1	1.420 (2)	C15—H15A	0.9600
C7—O1	1.235 (2)	C15—H15B	0.9600
C7—N1	1.336 (2)	C15—H15C	0.9600
C7—C8	1.505 (3)	N1—HN1	0.91 (2)
C8—C9	1.346 (3)	N2—HN2	0.89 (2)
C8—C14	1.465 (3)	OW1—HW1	0.92 (3)
C9—C10	1.427 (3)	OW1—HW2	0.87 (3)

C2—C1—C6	119.7 (2)	N2—C10—C9	119.18 (18)
C2—C1—H1	120.2	C11—C10—C9	134.50 (19)
C6—C1—H1	120.2	C10—C11—C12	107.6 (2)
C3—C2—C1	120.7 (2)	C10—C11—H11	126.2
C3—C2—H2	119.7	C12—C11—H11	126.2
C1—C2—H2	119.7	C13—C12—C11	107.8 (2)
C4—C3—C2	119.5 (2)	C13—C12—H12	126.1
C4—C3—H3	120.3	C11—C12—H12	126.1
C2—C3—H3	120.3	N2—C13—C12	108.4 (2)
C3—C4—C5	120.6 (2)	N2—C13—H13	125.8
C3—C4—H4	119.7	C12—C13—H13	125.8
C5—C4—H4	119.7	O2—C14—C8	118.96 (18)
C6—C5—C4	119.9 (2)	O2—C14—C15	120.36 (19)
C6—C5—H5	120.0	C8—C14—C15	120.68 (19)
C4—C5—H5	120.0	C14—C15—H15A	109.5
C5—C6—C1	119.57 (18)	C14—C15—H15B	109.5
C5—C6—N1	123.05 (18)	H15A—C15—H15B	109.5
C1—C6—N1	117.37 (17)	C14—C15—H15C	109.5
O1—C7—N1	124.06 (18)	H15A—C15—H15C	109.5
O1—C7—C8	121.43 (16)	H15B—C15—H15C	109.5
N1—C7—C8	114.50 (16)	C7—N1—C6	127.24 (17)
C9—C8—C14	122.57 (18)	C7—N1—HN1	114.1 (13)
C9—C8—C7	123.00 (17)	C6—N1—HN1	117.9 (13)
C14—C8—C7	114.39 (16)	C13—N2—C10	109.86 (18)
C8—C9—C10	128.81 (18)	C13—N2—HN2	125.1 (15)
C8—C9—H9	115.6	C10—N2—HN2	125.0 (15)
C10—C9—H9	115.6	HW1—OW1—HW2	109 (2)
N2—C10—C11	106.30 (18)

C6—C1—C2—C3	−0.6 (4)	N2—C10—C11—C12	−1.0 (2)
C1—C2—C3—C4	−1.2 (4)	C9—C10—C11—C12	177.1 (2)
C2—C3—C4—C5	1.5 (4)	C10—C11—C12—C13	0.4 (3)
C3—C4—C5—C6	−0.1 (4)	C11—C12—C13—N2	0.3 (3)
C4—C5—C6—C1	−1.6 (3)	C9—C8—C14—O2	−173.92 (19)
C4—C5—C6—N1	178.9 (2)	C7—C8—C14—O2	3.9 (3)
C2—C1—C6—C5	2.0 (3)	C9—C8—C14—C15	6.2 (3)
C2—C1—C6—N1	−178.5 (2)	C7—C8—C14—C15	−176.03 (18)
O1—C7—C8—C9	84.1 (2)	O1—C7—N1—C6	6.7 (3)
N1—C7—C8—C9	−97.0 (2)	C8—C7—N1—C6	−172.19 (17)
O1—C7—C8—C14	−93.7 (2)	C5—C6—N1—C7	−30.7 (3)
N1—C7—C8—C14	85.2 (2)	C1—C6—N1—C7	149.9 (2)
C14—C8—C9—C10	179.17 (18)	C12—C13—N2—C10	−1.0 (3)
C7—C8—C9—C10	1.5 (3)	C11—C10—N2—C13	1.2 (2)
C8—C9—C10—N2	176.92 (19)	C9—C10—N2—C13	−177.18 (17)
C8—C9—C10—C11	−1.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N2/C10–C13 pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.41	2.906 (3)	113
C13—H13···O1ⁱ	0.93	2.56	3.480 (3)	173
N1—HN1···OW1ⁱⁱ	0.91 (2)	1.99 (2)	2.898 (2)	179 (2)
N2—HN2···OW1ⁱⁱⁱ	0.89 (2)	2.02 (2)	2.901 (2)	173 (2)
OW1—HW1···O1	0.92 (3)	1.80 (3)	2.718 (2)	177 (2)
OW1—HW2···O2^iv	0.87 (3)	1.92 (3)	2.750 (2)	160 (2)
C15—H15C···Cg1ⁱⁱⁱ	0.96	2.66	3.536 (3)	151

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

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

Contact	Distance	Symmetry operation
O1···HW1	1.80	x, y, z
O1···H13	2.56	x, 1 + y, z
O2···HW2	1.92	3/2 - x, 3/2 - y, 1/2 - z
HN1···OW1	1.99	-1/2 + x, 1 - y, z
N2···H15B	2.92	1 - x, -1/2 + y, 1/2 - z
HN2···OW1	2.02	3/2 - x, 1/2 - y, 1/2 - z
H15C···N2	2.76	3/2 - x, 1/2 - y, 1/2 - z
H5···H5	2.36	3/2 - x, y, 1 - z
H3···C11	3.06	1 - x, 1 - y, 1 - z
H3···H15A	2.59	x, 3/2 - y, 1/2 + z

Acknowledgements

Authors' contributions are as follows. Conceptualization, ASS, ANK and FNN; methodology, ASS, ANK and MA; investigation, ASS and IB; writing (original draft), MA and AB; writing (review and editing of the manuscript), MA and ASS; visualization, MA and IB; funding acquisition, ASS, AB and IB; resources, AB, IB and MA; supervision, MA and IGM.

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Volume 79| Part 12| December 2023| Pages 1142-1146

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure and Hirshfeld surface analysis of (2Z)-3-oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methyl­idene]butanamide monohydrate

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure and Hirshfeld surface analysis of (2Z)-3-oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methylidene]butanamide monohydrate

3. Supramolecular features and Hirshfeld surface analysis