Crystal structure and Hirshfeld surface analysis of 4-(2-chloro­eth­yl)-5-methyl-1,2-di­hydro­pyrazol-3-one

In the crystal, mol­ecular pairs form dimers through N—H⋯O hydrogen bonds. These dimers are linked into ribbons parallel to the (100) plane by further N—H⋯O hydrogen bonds. In addition, π–π and C—Cl⋯π inter­actions between the ribbons form layers parallel to the (100) plane.

Computing details

4-(2-Chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one

Crystal data

C6H9ClN2O	F(000) = 336
Mr = 160.60	Dx = 1.405 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.8420 (2) Å	Cell parameters from 4592 reflections
b = 6.9145 (2) Å	θ = 4.5–77.6°
c = 11.1807 (2) Å	µ = 3.92 mm^−1
β = 93.618 (2)°	T = 100 K
V = 759.36 (3) Å^3	Prism, colourless
Z = 4	0.20 × 0.12 × 0.06 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	1467 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	Rint = 0.027
ω scans	θmax = 77.5°, θmin = 4.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −12→12
Tmin = 0.513, Tmax = 0.750	k = −8→7
6642 measured reflections	l = −14→8
1532 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: difference Fourier map
wR(F^2) = 0.097	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.606P] where P = (Fo^2 + 2Fc^2)/3
1532 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.45324 (5)	0.61848 (7)	0.86496 (4)	0.03447 (18)
O1	0.06705 (13)	0.89161 (17)	0.64445 (10)	0.0231 (3)
N1	0.05777 (14)	0.7905 (2)	0.44644 (12)	0.0197 (3)
H1	0.013 (3)	0.890 (4)	0.413 (2)	0.040 (7)*
N2	0.11129 (14)	0.6437 (2)	0.38217 (12)	0.0195 (3)
H2	0.096 (2)	0.636 (3)	0.300 (2)	0.038 (6)*
C3	0.18687 (16)	0.5302 (2)	0.45765 (14)	0.0189 (3)
C4	0.18362 (16)	0.6035 (2)	0.57245 (14)	0.0181 (3)
C5	0.10154 (16)	0.7717 (2)	0.56311 (13)	0.0188 (3)
C6	0.2560 (2)	0.3553 (3)	0.41307 (16)	0.0254 (4)
H6A	0.282 (3)	0.372 (4)	0.331 (3)	0.058 (8)*
H6B	0.338 (3)	0.328 (5)	0.458 (3)	0.065 (9)*
H6C	0.205 (3)	0.250 (5)	0.414 (3)	0.066 (9)*
C7	0.25721 (17)	0.5342 (2)	0.68559 (14)	0.0205 (3)
H7A	0.194 (2)	0.527 (3)	0.7508 (18)	0.021 (5)*
H7B	0.295 (2)	0.406 (3)	0.676 (2)	0.029 (5)*
C8	0.37260 (18)	0.6724 (3)	0.71941 (16)	0.0254 (4)
H8A	0.340 (2)	0.807 (4)	0.724 (2)	0.031 (6)*
H8B	0.443 (2)	0.665 (4)	0.664 (2)	0.037 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0401 (3)	0.0366 (3)	0.0249 (3)	0.00431 (18)	−0.01242 (19)	−0.00157 (17)
O1	0.0374 (7)	0.0209 (6)	0.0110 (5)	0.0082 (5)	0.0007 (5)	−0.0010 (4)
N1	0.0297 (7)	0.0180 (7)	0.0114 (6)	0.0045 (5)	0.0008 (5)	−0.0006 (5)
N2	0.0278 (7)	0.0194 (7)	0.0115 (7)	0.0026 (5)	0.0013 (5)	−0.0028 (5)
C3	0.0237 (7)	0.0179 (7)	0.0153 (7)	−0.0011 (6)	0.0027 (6)	0.0008 (6)
C4	0.0238 (7)	0.0177 (7)	0.0128 (7)	0.0008 (6)	0.0024 (6)	0.0017 (6)
C5	0.0273 (8)	0.0183 (7)	0.0110 (7)	−0.0002 (6)	0.0023 (6)	0.0003 (6)
C6	0.0333 (9)	0.0233 (8)	0.0198 (9)	0.0057 (7)	0.0033 (7)	−0.0036 (7)
C7	0.0280 (8)	0.0192 (8)	0.0144 (8)	0.0036 (6)	0.0015 (6)	0.0016 (6)
C8	0.0264 (8)	0.0315 (9)	0.0180 (8)	0.0006 (7)	−0.0019 (6)	0.0029 (7)

Geometric parameters (Å, º)

Cl1—C8	1.8040 (18)	C4—C7	1.496 (2)
O1—C5	1.2920 (19)	C6—H6A	0.97 (3)
N1—C5	1.354 (2)	C6—H6B	0.95 (3)
N1—N2	1.3685 (19)	C6—H6C	0.88 (3)
N1—H1	0.88 (3)	C7—C8	1.514 (2)
N2—C3	1.342 (2)	C7—H7A	0.99 (2)
N2—H2	0.92 (3)	C7—H7B	0.97 (2)
C3—C4	1.382 (2)	C8—H8A	0.99 (2)
C3—C6	1.489 (2)	C8—H8B	0.95 (2)
C4—C5	1.416 (2)
C5—N1—N2	108.95 (13)	H6A—C6—H6B	105 (2)
C5—N1—H1	126.8 (17)	C3—C6—H6C	113 (2)
N2—N1—H1	123.6 (17)	H6A—C6—H6C	107 (3)
C3—N2—N1	108.66 (13)	H6B—C6—H6C	107 (3)
C3—N2—H2	129.9 (15)	C4—C7—C8	108.91 (14)
N1—N2—H2	121.4 (15)	C4—C7—H7A	110.2 (12)
N2—C3—C4	108.96 (14)	C8—C7—H7A	110.3 (12)
N2—C3—C6	120.74 (15)	C4—C7—H7B	111.5 (13)
C4—C3—C6	130.29 (15)	C8—C7—H7B	108.6 (13)
C3—C4—C5	106.22 (14)	H7A—C7—H7B	107.3 (18)
C3—C4—C7	128.97 (15)	C7—C8—Cl1	112.04 (12)
C5—C4—C7	124.69 (14)	C7—C8—H8A	111.5 (13)
O1—C5—N1	122.31 (15)	Cl1—C8—H8A	105.7 (13)
O1—C5—C4	130.49 (14)	C7—C8—H8B	111.5 (15)
N1—C5—C4	107.19 (13)	Cl1—C8—H8B	106.1 (15)
C3—C6—H6A	111.6 (17)	H8A—C8—H8B	109.7 (19)
C3—C6—H6B	111.9 (19)
C5—N1—N2—C3	0.98 (18)	N2—N1—C5—C4	−1.24 (18)
N1—N2—C3—C4	−0.30 (18)	C3—C4—C5—O1	179.99 (17)
N1—N2—C3—C6	178.79 (15)	C7—C4—C5—O1	−3.7 (3)
N2—C3—C4—C5	−0.45 (18)	C3—C4—C5—N1	1.04 (18)
C6—C3—C4—C5	−179.43 (17)	C7—C4—C5—N1	177.36 (15)
N2—C3—C4—C7	−176.56 (16)	C3—C4—C7—C8	105.67 (19)
C6—C3—C4—C7	4.5 (3)	C5—C4—C7—C8	−69.8 (2)
N2—N1—C5—O1	179.70 (15)	C4—C7—C8—Cl1	172.38 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88 (3)	1.81 (3)	2.6861 (18)	174 (2)
N2—H2···O1^ii	0.92 (3)	1.75 (3)	2.6772 (17)	177 (2)

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