Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thia­zol-5-yl)ethan-1-one

In the crystal, pairs of mol­ecules are linked by N—H...N hydrogen bonds, forming (8) ring motifs. Dimers are connected by N—H...O hydrogen bonds, forming layers parallel to the (102) plane. These layers are connected by C—H...π and C=O...π inter­actions, consolidating the mol­ecular packing.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.142
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.144
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00525 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.178 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.144 Report
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT V8.40B (Bruker, 2016); data reduction: SAINT V8.40B (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

1-(2-Amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Crystal data

C6H8N2OS	F(000) = 328
Mr = 156.20	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.7445 (15) Å	Cell parameters from 2051 reflections
b = 13.498 (3) Å	θ = 3.0–26.4°
c = 8.010 (2) Å	µ = 0.37 mm^−1
β = 94.421 (7)°	T = 296 K
V = 727.1 (3) Å^3	Prism, colourless
Z = 4	0.60 × 0.45 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer	940 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.144
Absorption correction: multi-scan (SADABS; Krause et al., 2015	θmax = 26.4°, θmin = 3.0°
Tmin = 0.649, Tmax = 0.745	h = −8→8
14701 measured reflections	k = −16→16
1492 independent reflections	l = −10→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 0.4474P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1492 reflections	Δρmax = 0.29 e Å^−3
93 parameters	Δρmin = −0.28 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
C1	0.5920 (5)	0.7303 (2)	0.4486 (4)	0.0354 (8)
C2	0.7302 (5)	0.5848 (2)	0.4036 (4)	0.0356 (8)
C3	0.7583 (5)	0.7636 (2)	0.3769 (4)	0.0349 (8)
C4	0.4274 (5)	0.7905 (3)	0.5084 (5)	0.0446 (9)
H4A	0.356539	0.822440	0.414759	0.067*
H4B	0.480953	0.839710	0.585759	0.067*
H4C	0.338231	0.748209	0.563299	0.067*
C5	0.8348 (5)	0.8605 (3)	0.3393 (4)	0.0408 (9)
C6	0.7269 (6)	0.9538 (3)	0.3790 (5)	0.0567 (11)
H6A	0.718170	0.958584	0.497742	0.085*
H6B	0.595477	0.952624	0.323674	0.085*
H6C	0.798079	1.010036	0.340806	0.085*
N1	0.5761 (4)	0.62959 (19)	0.4631 (4)	0.0359 (7)
N2	0.7505 (4)	0.4865 (2)	0.4051 (4)	0.0498 (9)
H1A	0.661573	0.449933	0.445684	0.060*
H1B	0.852593	0.459698	0.365376	0.060*
S1	0.90402 (13)	0.66254 (6)	0.32437 (12)	0.0412 (3)
O1	0.9925 (4)	0.8657 (2)	0.2713 (4)	0.0571 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0349 (18)	0.0323 (17)	0.039 (2)	0.0005 (15)	0.0045 (15)	−0.0011 (15)
C2	0.0348 (18)	0.0287 (16)	0.044 (2)	0.0034 (14)	0.0063 (15)	0.0031 (15)
C3	0.0343 (18)	0.0308 (17)	0.040 (2)	−0.0023 (14)	0.0035 (15)	0.0009 (15)
C4	0.042 (2)	0.0320 (18)	0.061 (2)	0.0032 (16)	0.0105 (18)	−0.0005 (17)
C5	0.0410 (19)	0.0351 (19)	0.046 (2)	−0.0044 (15)	0.0016 (17)	0.0066 (15)
C6	0.066 (3)	0.0313 (19)	0.075 (3)	0.0012 (19)	0.015 (2)	0.0054 (19)
N1	0.0318 (14)	0.0294 (14)	0.0476 (18)	−0.0007 (11)	0.0093 (13)	0.0001 (13)
N2	0.0450 (18)	0.0295 (16)	0.078 (2)	0.0006 (13)	0.0263 (17)	0.0004 (15)
S1	0.0371 (5)	0.0341 (5)	0.0547 (6)	0.0002 (4)	0.0172 (4)	0.0035 (4)
O1	0.0474 (16)	0.0460 (16)	0.080 (2)	−0.0083 (12)	0.0182 (15)	0.0148 (14)

Geometric parameters (Å, º)

C1—N1	1.370 (4)	C4—H4B	0.9600
C1—C3	1.375 (4)	C4—H4C	0.9600
C1—C4	1.484 (5)	C5—O1	1.234 (4)
C2—N1	1.322 (4)	C5—C6	1.501 (5)
C2—N2	1.334 (4)	C6—H6A	0.9600
C2—S1	1.730 (3)	C6—H6B	0.9600
C3—C5	1.446 (5)	C6—H6C	0.9600
C3—S1	1.752 (3)	N2—H1A	0.8600
C4—H4A	0.9600	N2—H1B	0.8600
N1—C1—C3	115.6 (3)	O1—C5—C3	118.5 (3)
N1—C1—C4	116.8 (3)	O1—C5—C6	119.6 (3)
C3—C1—C4	127.6 (3)	C3—C5—C6	121.9 (3)
N1—C2—N2	122.3 (3)	C5—C6—H6A	109.5
N1—C2—S1	115.4 (2)	C5—C6—H6B	109.5
N2—C2—S1	122.3 (2)	H6A—C6—H6B	109.5
C1—C3—C5	134.3 (3)	C5—C6—H6C	109.5
C1—C3—S1	109.7 (2)	H6A—C6—H6C	109.5
C5—C3—S1	116.0 (2)	H6B—C6—H6C	109.5
C1—C4—H4A	109.5	C2—N1—C1	110.7 (3)
C1—C4—H4B	109.5	C2—N2—H1A	120.0
H4A—C4—H4B	109.5	C2—N2—H1B	120.0
C1—C4—H4C	109.5	H1A—N2—H1B	120.0
H4A—C4—H4C	109.5	C2—S1—C3	88.60 (15)
H4B—C4—H4C	109.5
N1—C1—C3—C5	−179.3 (4)	N2—C2—N1—C1	179.3 (3)
C4—C1—C3—C5	2.0 (7)	S1—C2—N1—C1	−0.5 (4)
N1—C1—C3—S1	0.0 (4)	C3—C1—N1—C2	0.3 (5)
C4—C1—C3—S1	−178.7 (3)	C4—C1—N1—C2	179.2 (3)
C1—C3—C5—O1	−179.5 (4)	N1—C2—S1—C3	0.4 (3)
S1—C3—C5—O1	1.3 (5)	N2—C2—S1—C3	−179.4 (3)
C1—C3—C5—C6	−0.1 (7)	C1—C3—S1—C2	−0.2 (3)
S1—C3—C5—C6	−179.4 (3)	C5—C3—S1—C2	179.2 (3)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the (N1/S1/C1–C3) 1,3-thiazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···N1^i	0.86	2.11	2.963 (4)	175
N2—H1B···O1^ii	0.86	2.02	2.835 (4)	158
C4—H4B···Cg1^iii	0.96	2.89	3.603 (4)	132

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