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

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

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

In the title compound, the molecules are connected by C—H

O hydrogen bonds in layers parallel to the (020) plane. C—H

π and π–π interactions further link the molecules into chains extending in the [ $\overline{1}$ 01] direction.

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

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009799/vm2291sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009799/vm2291Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009799/vm2291Isup3.cml Supplementary material

CCDC reference: 2306713

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

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