Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methylsulfanyl)phenyl]acetamide (2024)

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020002960/zq2250sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020002960/zq2250Isup3.hkl Contains datablock I

CCDC reference: 1987798

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.127
Data-to-parameter ratio = 19.8

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No syntax errors foundAlert level CPLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.852 CheckPLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 ReportAlert level GPLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 NotePLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info 0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, checkcheckCIF publication errorsAlert level APUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper. 1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009) andMercury (Macrae et al., 2020); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) andMercury (Macrae et al., 2020).

2-Chloro-N-[4-(methylsulfanyl)phenyl]acetamide top

Crystal data

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C₉H₁₀ClNOS	D_x = 1.454 Mg m⁻³
M_r = 215.69	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3435 reflections
a = 9.6659 (7) Å	θ = 2.8–26.2°
b = 14.0682 (11) Å	µ = 0.56 mm⁻¹
c = 14.4869 (13) Å	T = 296 K
V = 1970.0 (3) Å³	Block, light brown
Z = 8	0.12 × 0.10 × 0.08 mm
F(000) = 896

Data collection

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Bruker APEXII CCD diffractometer	1722 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.085
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 28.3°, θ_min = 2.8°
T_min = 0.686, T_max = 0.746	h = −12→12
21994 measured reflections	k = −18→17
2438 independent reflections	l = −19→17

Refinement

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Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.051P)² + 1.0616P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2438 reflections	Δρ_max = 0.51 e Å⁻³
123 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints

Special details

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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)

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	x	y	z	U_iso*/U_eq
Cl1	0.44778 (8)	0.40070 (6)	0.90711 (5)	0.0685 (3)
S1	0.52668 (8)	0.73979 (6)	0.33195 (5)	0.0612 (2)
O1	0.36226 (15)	0.51663 (13)	0.74128 (12)	0.0498 (4)
N1	0.58369 (17)	0.53698 (14)	0.69210 (13)	0.0364 (4)
H1	0.663 (3)	0.5277 (17)	0.7080 (18)	0.044*
C3	0.56559 (19)	0.58332 (15)	0.60636 (15)	0.0333 (4)
C7	0.6767 (2)	0.66353 (17)	0.47953 (16)	0.0423 (5)
H7	0.757186	0.685406	0.451533	0.051*
C2	0.4871 (2)	0.51212 (16)	0.75445 (16)	0.0370 (5)
C8	0.6844 (2)	0.61629 (17)	0.56270 (16)	0.0394 (5)
H8	0.770224	0.606313	0.590012	0.047*
C6	0.5498 (2)	0.67873 (16)	0.43719 (16)	0.0392 (5)
C4	0.4384 (2)	0.59718 (17)	0.56390 (17)	0.0404 (5)
H4	0.357922	0.574908	0.591632	0.048*
C5	0.4319 (2)	0.64410 (18)	0.48042 (17)	0.0440 (5)
H5	0.346335	0.652779	0.452346	0.053*
C1	0.5487 (2)	0.4838 (2)	0.84654 (17)	0.0477 (6)
H1A	0.559753	0.540211	0.884279	0.057*
H1B	0.639951	0.457030	0.836228	0.057*
C9	0.6958 (3)	0.7388 (2)	0.28174 (19)	0.0566 (7)
H9A	0.691402	0.764360	0.220355	0.085*
H9B	0.729678	0.674728	0.279361	0.085*
H9C	0.757047	0.776878	0.318558	0.085*

Atomic displacement parameters (Å²)

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	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0643 (5)	0.0892 (6)	0.0520 (4)	−0.0232 (4)	0.0053 (3)	0.0168 (4)
S1	0.0566 (4)	0.0723 (5)	0.0548 (4)	0.0139 (3)	−0.0006 (3)	0.0206 (4)
O1	0.0241 (7)	0.0781 (12)	0.0471 (10)	−0.0002 (7)	0.0034 (6)	0.0045 (9)
N1	0.0227 (8)	0.0513 (11)	0.0353 (10)	−0.0003 (7)	0.0005 (7)	−0.0016 (8)
C3	0.0295 (9)	0.0378 (11)	0.0327 (11)	0.0009 (8)	−0.0001 (8)	−0.0055 (9)
C7	0.0332 (11)	0.0514 (14)	0.0423 (13)	−0.0058 (9)	0.0034 (9)	0.0001 (11)
C2	0.0279 (10)	0.0441 (12)	0.0389 (12)	−0.0001 (8)	0.0028 (8)	−0.0050 (10)
C8	0.0274 (10)	0.0517 (14)	0.0391 (12)	−0.0021 (9)	−0.0020 (8)	−0.0020 (10)
C6	0.0400 (12)	0.0391 (12)	0.0385 (12)	0.0028 (9)	−0.0003 (9)	−0.0021 (10)
C4	0.0266 (10)	0.0506 (13)	0.0440 (13)	−0.0006 (9)	0.0008 (9)	−0.0011 (10)
C5	0.0299 (10)	0.0548 (14)	0.0475 (14)	0.0058 (9)	−0.0057 (9)	−0.0015 (11)
C1	0.0348 (11)	0.0638 (16)	0.0444 (14)	−0.0040 (10)	0.0040 (10)	0.0069 (12)
C9	0.0628 (16)	0.0592 (17)	0.0478 (15)	−0.0048 (12)	0.0032 (12)	0.0110 (12)

Geometric parameters (Å, º)

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Cl1—C1	1.757 (2)	C2—C1	1.515 (3)
S1—C6	1.764 (2)	C8—H8	0.9300
S1—C9	1.789 (3)	C6—C5	1.388 (3)
O1—C2	1.223 (2)	C4—H4	0.9300
N1—H1	0.82 (2)	C4—C5	1.379 (3)
N1—C3	1.414 (3)	C5—H5	0.9300
N1—C2	1.345 (3)	C1—H1A	0.9700
C3—C8	1.390 (3)	C1—H1B	0.9700
C3—C4	1.388 (3)	C9—H9A	0.9600
C7—H7	0.9300	C9—H9B	0.9600
C7—C8	1.378 (3)	C9—H9C	0.9600
C7—C6	1.388 (3)

C6—S1—C9	103.42 (12)	C3—C4—H4	120.1
C3—N1—H1	116.1 (19)	C5—C4—C3	119.7 (2)
C2—N1—H1	115.1 (18)	C5—C4—H4	120.1
C2—N1—C3	128.60 (18)	C6—C5—H5	119.1
C8—C3—N1	116.83 (18)	C4—C5—C6	121.8 (2)
C4—C3—N1	124.31 (18)	C4—C5—H5	119.1
C4—C3—C8	118.9 (2)	Cl1—C1—H1A	108.9
C8—C7—H7	119.7	Cl1—C1—H1B	108.9
C8—C7—C6	120.6 (2)	C2—C1—Cl1	113.36 (16)
C6—C7—H7	119.7	C2—C1—H1A	108.9
O1—C2—N1	124.5 (2)	C2—C1—H1B	108.9
O1—C2—C1	122.62 (19)	H1A—C1—H1B	107.7
N1—C2—C1	112.76 (18)	S1—C9—H9A	109.5
C3—C8—H8	119.5	S1—C9—H9B	109.5
C7—C8—C3	120.9 (2)	S1—C9—H9C	109.5
C7—C8—H8	119.5	H9A—C9—H9B	109.5
C7—C6—S1	124.67 (18)	H9A—C9—H9C	109.5
C7—C6—C5	118.1 (2)	H9B—C9—H9C	109.5
C5—C6—S1	117.19 (17)

S1—C6—C5—C4	−178.58 (19)	C2—N1—C3—C8	168.6 (2)
O1—C2—C1—Cl1	32.9 (3)	C2—N1—C3—C4	−11.7 (4)
N1—C3—C8—C7	−179.1 (2)	C8—C3—C4—C5	−0.8 (3)
N1—C3—C4—C5	179.4 (2)	C8—C7—C6—S1	178.92 (18)
N1—C2—C1—Cl1	−150.97 (18)	C8—C7—C6—C5	−0.7 (4)
C3—N1—C2—O1	8.9 (4)	C6—C7—C8—C3	−0.4 (4)
C3—N1—C2—C1	−167.2 (2)	C4—C3—C8—C7	1.2 (3)
C3—C4—C5—C6	−0.3 (4)	C9—S1—C6—C7	18.0 (2)
C7—C6—C5—C4	1.1 (4)	C9—S1—C6—C5	−162.3 (2)

Hydrogen-bond geometry (Å, º)

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D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.82 (2)	2.06 (3)	2.875 (2)	174 (3)
C1—H1B···O1ⁱ	0.97	2.57	3.319 (3)	135
C4—H4···O1	0.93	2.32	2.903 (3)	121

Symmetry code: (i) x+1/2, y, −z+3/2.

The electronic absorption spectrum of the title compound calculated by the TD-CAM-B3LYP/6-311G(d,p) method

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Excited states		Excitation energy		Configurations composition
	eV	nm	f
S₀→S₁	4.80	258	0.0354	hom*o→L+1 (84%)
S₀→S₂	4.95	250	0.7144	hom*o→LUMO (91%)
S₀→S₃	5.55	224	0.0000	hom*o→L+3 (81%)
S₀→S₄	5.63	220	0.0005	H-3→LUMO (69%)
S₀→S₅	6.35	195	0.1378	H-1→LUMO (59%)

Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methyl­sulfan­yl)phen­yl]acetamide (2024)

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methylsulfanyl)phenyl]acetamide (2024)