Crystal structure and Hirshfeld surface analysis of 2-chloro-N-(4-meth­oxy­phen­yl)acetamide

Missioui, M.; Guerrab, W.; Nchioua, I.; El Moutaouakil Ala Allah, A.; Kalonji Mubengayi, C.; Alsubari, A.; Mague, J.T.; Ramli, Y.

doi:10.1107/S205698902200576X

research communications

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ISSN: 2056-9890

Volume 78| Part 7| July 2022| Pages 687-690

https://doi.org/10.1107/S205698902200576X

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Crystal structure and Hirshfeld surface analysis of 2-chloro-N-(4-methoxyphenyl)acetamide

Mohcine Missioui,^a Walid Guerrab,^a Intissar Nchioua,^a Abderrazzak El Moutaouakil Ala Allah,^a Camille Kalonji Mubengayi,^b Abdulsalam Alsubari,^c ^* Joel T. Mague ^d and Youssef Ramli ^a ^*

^aLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco, ^bLaboratoire de Chimie et Biochimie, Institut Superieur des Techniques Medicales de Kinshasa, Republique Democratique du , Congo, ^cLaboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21 September University, Yemen, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: alsubaripharmaco@21umas.edu.ye, y.ramli@um5r.ac.ma

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 18 May 2022; accepted 28 May 2022; online 7 June 2022)

In the title molecule, C₉H₁₀ClNO₂, the methoxy group lies very close to the plane of the phenyl ring while the acetamido group is twisted out of this plane by 28.87 (5)°. In the crystal, a three-dimensional structure is generated by N—H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds plus C—H⋯π(ring) interactions. A Hirshfeld surface analysis of the intermolecular interactions was performed and indicated that C⋯H/H⋯C interactions make the largest contribution to the surface area (33.4%).

Keywords: crystal structure; hydrogen bond; C—H⋯π(ring) interaction; acetamide; Hirshfeld surface.

CCDC reference: 2175514

1. Chemical context

Amides play a very important role in organic synthesis, including the production of medicines, functional materials, and bioactive molecules (Alcaide et al., 2007 ; Zhang et al., 2012 ; García-Álvarez et al., 2013 ; Ramli & Essassi, 2015 ; Álvarez-Pérez et al., 2019 ). In particular, N-arylacetamides are significant intermediates for the synthesis of medicinal, agrochemical, and pharmaceutical compounds (Beccalli et al., 2007 ; Valeur & Bradley, 2009 ; Allen & Williams, 2011 ; Missioui et al., 2021 , 2022a ,b ,c ). Given the wide range of therapeutic applications for such compounds, and in a continuation of our research efforts to synthesize more N-arylacetamides (Missioui et al., 2020 ; Guerrab et al., 2021 ), we report the synthesis, molecular and crystal structure and Hirshfeld surface analysis of the title compound, 2-chloro-N-(4-methoxyphenyl)acetamide.

2. Structural commentary

The methoxy group lies close to the mean plane of the phenyl ring C3–C8, as indicated by the C7—C6—O2—C9 torsion angle of −174.61 (10)° and atom C9 deviating by only 0.065 (1) Å from the mean plane through the C3–C8 ring. In contrast, the acetamido group is rotated out of the above plane with the dihedral angle between the mean plane through the C3–C8 ring and that defined by N1/C2/C1/O1 being 28.87 (5)° (Fig. 1). The sum of the angles about N1 is 360.0 (9)°, indicating it to be planar (sp² hybridization). The Cl1—C1—C2—O1 torsion angle is 52.89 (12)°, illustrating a + synclinal (+ gauche) conformation about the C1—C2 bond. This places atom Cl1 at 1.299 (1) Å from the plane defined by C1, C2, N1 and O1.

Figure 1
The molecular structure of the title molecule with labelling scheme and 50% probability ellipsoids.

3. Supramolecular features

In the crystal, N1—H1⋯O1 hydrogen bonds (Table 1) form helical chains along the 2₁ axes. These chains are linked by C1—H1A⋯O2 hydrogen bonds (Table 1), forming layers of molecules parallel to the ab plane (Fig. 2). The layers are linked by weak C4—H4⋯Cl1 hydrogen bonds as well as by C9—H9B⋯Cg1 interactions (Table 1) to generate the final three-dimensional structure (Fig. 3). As the shortest distance between parallel phenyl rings is 5.1075 (7) Å, there are no π–π stacking interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.89 (1)	2.01 (1)	2.8910 (11)	171 (1)
C1—H1A⋯O2ⁱⁱ	0.99	2.48	3.3347 (13)	145
C4—H4⋯Cl1ⁱⁱⁱ	0.95	2.83	3.7646 (10)	167
C9—H9B⋯Cg1^iv	0.98	2.72	3.5020 (13)	137
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Figure 2
A portion of one layer of the crystal packing viewed along the c-axis direction with N—H⋯O and C—H⋯O hydrogen bonds depicted, respectively, by violet and black dashed lines. Non-interacting hydrogen atoms are omitted for clarity.

Figure 3
Packing viewed along the a-axis direction with N—H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds depicted, respectively by violet, black and light green dashed lines. C—H⋯π(ring) interactions are depicted by brown dashed lines and non-interacting hydrogen atoms are omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to March 2022; Groom et al., 2016 ) using the fragment A (Fig. 4, R = undefined, X = halogen) yielded 15 hits of which 13 had X = Cl and R = OEt (DELZIE; Zhang et al., 2006 ), COOEt (HEGLOW; Behbehani & Ibrahim, 2012 ), F (JODQEZ; Kang et al., 2008 ), S(O)₂NH(C₃HNO(CH₃)) (NULZEC; Murtaza et al., 2019 ), SO₂NH₂ (PINXAO; Florke & Saeed, 2018 ; QUYRIM; Akkurt et al., 2010 ), SMe (QUGTEU; Mongkholkeaw et al., 2020 ), H (RIYWIG; Gowda et al., 2008 ), NO₂ (WEPGEE; Wen et al., 2006 ; WEPGEE01; Gowda et al., 2007a ), Cl (WINSUI; Gowda et al., 2007b ), MeC(=O) (XABWEF; Ashraf et al., 2016 ) and Me (XICMAY; Gowda et al., 2007c ). The last two hits had X = Br and R = Br (FOWYIA; Gowda et al., 2009 ) and CH₂CH₂O₂CC(F)(SPh)(NO₂) (VAGCOV; Takeuchi et al., 1988 ). In general, the conformation of the haloacetamide portion is quite similar in all structures, as is the formation of infinite chains by N—H⋯O hydrogen bonds and these are comparable to the features found in the title structure. In DELZIE and XABWEF, C—H⋯π(ring) interactions assist in the packing, as also observed for the title molecule.

Figure 4
Fragment A used in the Cambridge Structural Database search.

5. Hirshfeld surface analysis

The analysis was performed with CrystalExplorer 21.5 (Spackman et al., 2021 ) with the details of the pictorial output described in a recent publication (Tan et al., 2019 ). Fig. 5 shows the d_norm surface for the asymmetric unit plotted over the range −0.5547 to 0.9665 arbitrary units together with two adjacent molecules that are part of one infinite chain and two in adjacent chains (cf. Fig. 2). The bright-red spots at the top and bottom indicate the N—H⋯O hydrogen bonds (blue arrows) while the fainter ones at the far right and left indicate the C— H⋯O hydrogen bonds linking the chains (curved black lines) while that below and to the right of the Cl atom represents the weak C—H⋯Cl hydrogen bonds. Fig. 6a is the fingerprint plot showing all intermolecular interactions while Fig. 6b–6d show these resolved into C⋯H/H⋯C (33.4%), O⋯H/H⋯O (19.5%) and Cl⋯H/H⋯Cl (20%) interactions, respectively.

Figure 5
The Hirshfeld surface of the title molecule with two adjacent molecules involved in the N—H⋯O, hydrogen bonded chain and two involving the C1—H1A⋯O2 hydrogen bonds. The former interaction is depicted by blue arrows and the latter by curved black lines.

Figure 6
Fingerprint plots for the title molecule: (a), all intermolecular interactions; (b), C⋯H/H⋯C interactions; (c), O⋯H/H⋯O interactions; (d), Cl⋯H/H⋯Cl interactions.

6. Synthesis and crystallization

0.047 mol of 4-methoxyaniline were dissolved in 40 mL of pure acetic acid and put in an ice bath. Subsequently, chloroacetyl chloride (0.047 mol) was added portionwise under stirring. At the end of the reaction, a solution of sodium acetate (35 mL) was added and a solid precipitate appeared after 30 min of stirring at room temperature. The resulting solid was filtered and washed with cold water, dried and recrystallized from ethanol to give the title compound as colourless crystals.

Yield 80%, m.p. = 398.6–400.3 K, FT–IR (ATR, υ, cm⁻¹) 3292 (υ N—H amide), 1029 (υ N—C amide), 1660 (υ C=O amide), 3073 (υ C—H_arom), 827 (υ C—Cl), 2959 (υ C—H,CH₂), ¹H NMR (DMSO–d₆) δ pm: 3.74 (3H, s, CH₃); 4.24 (2H, s, CH₂), 6.93–7.5 (4H, m, J = 1.3 Hz, H_arom), 10.23 (1H, s, NH), ¹³C NMR (DMSO–d₆) δ ppm: 43.48 (CH₂), 55.23 (CH₃), 131.53 (C_arom—N), 155.51 (C_arom—O), 113.92–120.92 (C_arom), 164.13 (C=O); HRMS (ESI–MS) (m/z) calculated for C₉H₁₀ClNO₂ 199.04, found 199.0105.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms attached to carbon were placed in idealized positions and included as riding contributions with isotropic displacement parameters fixed at 1.2U_eq(C) (1.5 for the methyl group). The N-bound H atom was found in a difference-Fourier map and refined with a DFIX 0.91 0.01 instruction and an independent isotropic displacement parameter.

Table 2
Experimental details

Crystal data
Chemical formula	C₉H₁₀ClNO₂
M_r	199.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	172
a, b, c (Å)	10.0939 (5), 9.6423 (5), 10.2799 (5)
β (°)	115.531 (2)
V (Å³)	902.83 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.39
Crystal size (mm)	0.29 × 0.25 × 0.09

Data collection
Diffractometer	Bruker D8 QUEST PHOTON 3 diffractometer
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.91, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	43210, 2871, 2508
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.726

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.10
No. of reflections	2871
No. of parameters	123
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2020 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2175514

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S205698902200576X/vm2264sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902200576X/vm2264Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902200576X/vm2264Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2020); cell refinement: SAINT (Bruker, 2020); data reduction: SAINT (Bruker, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-Chloro-N-(4-methoxyphenyl)acetamide top

Crystal data top

C₉H₁₀ClNO₂	F(000) = 416
M_r = 199.63	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0939 (5) Å	Cell parameters from 9903 reflections
b = 9.6423 (5) Å	θ = 2.2–31.1°
c = 10.2799 (5) Å	µ = 0.39 mm⁻¹
β = 115.531 (2)°	T = 172 K
V = 902.83 (8) Å³	Plate, colourless
Z = 4	0.29 × 0.25 × 0.09 mm

Data collection top

Bruker D8 QUEST PHOTON 3 diffractometer	2871 independent reflections
Radiation source: fine-focus sealed tube	2508 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 7.3910 pixels mm^-1	θ_max = 31.1°, θ_min = 3.1°
φ and ω scans	h = −14→14
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −13→13
T_min = 0.91, T_max = 0.97	l = −14→14
43210 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0462P)² + 0.2203P] where P = (F_o² + 2F_c²)/3
2871 reflections	(Δ/σ)_max = 0.001
123 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 7 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX3. The scan time was 6 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) and were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. That attached to nitrogen was placed in a location derived from a difference map and refined with a DFIX 0.91 0.01 instruction.

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

	x	y	z	U_iso*/U_eq
Cl1	0.30989 (3)	0.41222 (3)	0.90827 (3)	0.03169 (9)
O1	0.43630 (10)	0.27410 (8)	0.71560 (10)	0.03148 (19)
O2	0.99240 (9)	0.34016 (9)	0.56309 (9)	0.03316 (19)
N1	0.53618 (9)	0.48405 (8)	0.70583 (9)	0.02160 (17)
H1	0.5353 (17)	0.5749 (9)	0.7222 (16)	0.034 (4)*
C1	0.32272 (11)	0.47958 (10)	0.75260 (11)	0.02423 (19)
H1A	0.226444	0.470886	0.667909	0.029*
H1B	0.348725	0.579198	0.767150	0.029*
C2	0.43834 (11)	0.40146 (10)	0.72459 (10)	0.02147 (19)
C3	0.64850 (11)	0.44121 (10)	0.66649 (10)	0.02036 (18)
C4	0.63724 (11)	0.32251 (10)	0.58566 (11)	0.02264 (19)
H4	0.552126	0.265906	0.555512	0.027*
C5	0.75029 (11)	0.28609 (10)	0.54860 (10)	0.02332 (19)
H5	0.742024	0.204773	0.493437	0.028*
C6	0.87484 (11)	0.36845 (11)	0.59218 (11)	0.02389 (19)
C7	0.88452 (12)	0.48995 (11)	0.66987 (12)	0.0275 (2)
H7	0.968462	0.547843	0.697712	0.033*
C8	0.77218 (12)	0.52620 (10)	0.70637 (11)	0.0249 (2)
H8	0.779097	0.609174	0.758744	0.030*
C9	0.97987 (13)	0.22369 (13)	0.47330 (13)	0.0325 (2)
H9A	1.070019	0.214361	0.460154	0.049*
H9B	0.896160	0.237045	0.379304	0.049*
H9C	0.964803	0.139514	0.518658	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03574 (16)	0.03273 (15)	0.03447 (15)	0.00576 (10)	0.02258 (12)	0.00686 (10)
O1	0.0429 (5)	0.0163 (3)	0.0466 (5)	−0.0005 (3)	0.0300 (4)	0.0011 (3)
O2	0.0278 (4)	0.0390 (5)	0.0389 (4)	−0.0049 (3)	0.0202 (3)	−0.0107 (3)
N1	0.0247 (4)	0.0154 (4)	0.0269 (4)	−0.0001 (3)	0.0133 (3)	−0.0006 (3)
C1	0.0259 (5)	0.0214 (4)	0.0278 (5)	0.0031 (3)	0.0139 (4)	0.0043 (4)
C2	0.0253 (4)	0.0181 (4)	0.0226 (4)	0.0010 (3)	0.0118 (4)	0.0022 (3)
C3	0.0228 (4)	0.0177 (4)	0.0213 (4)	0.0002 (3)	0.0102 (3)	0.0013 (3)
C4	0.0239 (4)	0.0204 (4)	0.0240 (4)	−0.0033 (3)	0.0107 (3)	−0.0022 (3)
C5	0.0275 (5)	0.0206 (4)	0.0232 (4)	−0.0013 (3)	0.0121 (4)	−0.0027 (3)
C6	0.0252 (4)	0.0255 (5)	0.0229 (4)	−0.0010 (4)	0.0122 (4)	−0.0002 (3)
C7	0.0278 (5)	0.0256 (5)	0.0320 (5)	−0.0071 (4)	0.0156 (4)	−0.0051 (4)
C8	0.0286 (5)	0.0194 (4)	0.0283 (5)	−0.0041 (4)	0.0139 (4)	−0.0042 (3)
C9	0.0336 (6)	0.0345 (6)	0.0336 (6)	0.0051 (4)	0.0184 (5)	−0.0027 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7828 (10)	C4—C5	1.3947 (14)
O1—C2	1.2310 (12)	C4—H4	0.9500
O2—C6	1.3704 (13)	C5—C6	1.3880 (14)
O2—C9	1.4243 (14)	C5—H5	0.9500
N1—C2	1.3457 (13)	C6—C7	1.3973 (15)
N1—C3	1.4194 (13)	C7—C8	1.3840 (15)
N1—H1	0.893 (9)	C7—H7	0.9500
C1—C2	1.5172 (14)	C8—H8	0.9500
C1—H1A	0.9900	C9—H9A	0.9800
C1—H1B	0.9900	C9—H9B	0.9800
C3—C4	1.3900 (13)	C9—H9C	0.9800
C3—C8	1.3989 (14)

C6—O2—C9	117.06 (9)	C6—C5—C4	120.11 (9)
C2—N1—C3	126.46 (8)	C6—C5—H5	119.9
C2—N1—H1	119.0 (10)	C4—C5—H5	119.9
C3—N1—H1	114.5 (10)	O2—C6—C5	124.39 (9)
C2—C1—Cl1	110.42 (7)	O2—C6—C7	115.96 (9)
C2—C1—H1A	109.6	C5—C6—C7	119.65 (9)
Cl1—C1—H1A	109.6	C8—C7—C6	120.20 (9)
C2—C1—H1B	109.6	C8—C7—H7	119.9
Cl1—C1—H1B	109.6	C6—C7—H7	119.9
H1A—C1—H1B	108.1	C7—C8—C3	120.30 (9)
O1—C2—N1	124.69 (9)	C7—C8—H8	119.8
O1—C2—C1	121.35 (9)	C3—C8—H8	119.8
N1—C2—C1	113.91 (8)	O2—C9—H9A	109.5
C4—C3—C8	119.36 (9)	O2—C9—H9B	109.5
C4—C3—N1	122.71 (9)	H9A—C9—H9B	109.5
C8—C3—N1	117.88 (9)	O2—C9—H9C	109.5
C3—C4—C5	120.33 (9)	H9A—C9—H9C	109.5
C3—C4—H4	119.8	H9B—C9—H9C	109.5
C5—C4—H4	119.8

C3—N1—C2—O1	3.07 (17)	C9—O2—C6—C5	4.72 (16)
C3—N1—C2—C1	−174.47 (9)	C9—O2—C6—C7	−174.61 (10)
Cl1—C1—C2—O1	52.89 (12)	C4—C5—C6—O2	178.93 (10)
Cl1—C1—C2—N1	−129.47 (8)	C4—C5—C6—C7	−1.77 (15)
C2—N1—C3—C4	27.78 (15)	O2—C6—C7—C8	−179.00 (10)
C2—N1—C3—C8	−154.97 (10)	C5—C6—C7—C8	1.64 (16)
C8—C3—C4—C5	2.04 (15)	C6—C7—C8—C3	0.34 (16)
N1—C3—C4—C5	179.25 (9)	C4—C3—C8—C7	−2.17 (15)
C3—C4—C5—C6	−0.08 (15)	N1—C3—C8—C7	−179.52 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (1)	2.01 (1)	2.8910 (11)	171 (1)
C1—H1A···O2ⁱⁱ	0.99	2.48	3.3347 (13)	145
C4—H4···Cl1ⁱⁱⁱ	0.95	2.83	3.7646 (10)	167
C9—H9B···Cg1^iv	0.98	2.72	3.5020 (13)	137

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. Author contributions are as follows: conceptualization, YR; methodology, WG and CKM; investigation, IN, AEMAA and MM; theoretical calculations, JTM; writing (original draft), JTM and YR; writing (review and editing of the manuscript), YR; formal analysis, AA and MM; supervision, YR; crystal-structure determination and validation, JTM.

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Volume 78| Part 7| July 2022| Pages 687-690

https://doi.org/10.1107/S205698902200576X

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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 2-chloro-N-(4-meth­­oxy­phen­yl)acetamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure and Hirshfeld surface analysis of 2-chloro-N-(4-methoxyphenyl)acetamide

3. Supramolecular features