(E)-2-Acetyl-3-hydr­oxy-N-phenyl­but-2-enethio­amide

Xiao, H.-L.; Jian, F.-F.

doi:10.1107/S1600536806020216

(E)-2-Acetyl-3-hydroxy-N-phenylbut-2-enethioamide

The title compound, C₁₂H₁₃NO₂S, was prepared by the reaction of acetylacetone with phenyl isothiocyanate. In addition to the intramolecular O—H

O hydrogen bond, there is a weak intermolecular N—H

S hydrogen bond, which links the molecules into chains extended along the c axis. The crystal packing is further stabilized by van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020216/cv2062sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020216/cv2062Isup2.hkl Contains datablock I

CCDC reference: 613648

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.146
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.858(10) ......       4.00 su-Rat
              O2   -H2      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.858(10) ......       4.00 su-Rat
              O2   -H2      1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.98
           From the CIF: _reflns_number_total               2675
           Count of symmetry unique reflns         1549
           Completeness (_total/calc)            172.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1126
           Fraction of Friedel pairs measured     0.727
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-2-Acetyl-3-hydroxy-N-phenylbut-2-enethioamide top

Crystal data top

C₁₂H₁₃NO₂S	F(000) = 496
M_r = 235.29	D_x = 1.274 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 11.249 (2) Å	θ = 4–14°
b = 10.506 (2) Å	µ = 0.25 mm⁻¹
c = 10.376 (2) Å	T = 293 K
V = 1226.3 (4) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.043
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 2.7°
Graphite monochromator	h = −14→14
ω scans	k = −13→13
5616 measured reflections	l = 0→13
2675 independent reflections	3 standard reflections every 100 reflections
2117 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.1117P)² + 0.097P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.146	(Δ/σ)_max < 0.001
S = 0.94	Δρ_max = 0.37 e Å⁻³
2675 reflections	Δρ_min = −0.29 e Å⁻³
150 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.122 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1126 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.13 (13)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	U_iso*/U_eq
S1	0.16955 (6)	0.58156 (9)	1.06940 (6)	0.0664 (3)
O1	0.54099 (17)	0.5478 (3)	0.8619 (3)	0.0869 (9)
O2	0.5025 (2)	0.3352 (3)	0.9541 (3)	0.0890 (9)
N1	0.15784 (17)	0.4859 (2)	0.83058 (19)	0.0473 (5)
H1A	0.1999	0.4576	0.7676	0.057*
C1	−0.0449 (2)	0.5711 (3)	0.8645 (3)	0.0658 (8)
H1B	−0.0202	0.6229	0.9321	0.079*
C2	−0.1633 (2)	0.5720 (3)	0.8240 (4)	0.0717 (8)
H2A	−0.2174	0.6257	0.8645	0.086*
C3	−0.2008 (2)	0.4954 (3)	0.7262 (3)	0.0676 (8)
H3A	−0.2800	0.4969	0.7004	0.081*
C4	−0.1210 (3)	0.4156 (4)	0.6653 (3)	0.0710 (9)
H4A	−0.1463	0.3625	0.5991	0.085*
C5	−0.0051 (2)	0.4153 (3)	0.7029 (3)	0.0593 (7)
H5A	0.0487	0.3624	0.6609	0.071*
C6	0.0345 (2)	0.4927 (2)	0.8031 (2)	0.0461 (5)
C7	0.22133 (18)	0.5149 (2)	0.9355 (2)	0.0436 (5)
C8	0.3500 (2)	0.4823 (3)	0.9221 (2)	0.0492 (5)
C9	0.4301 (2)	0.5731 (4)	0.8716 (3)	0.0621 (7)
C10	0.3910 (3)	0.7012 (4)	0.8276 (4)	0.0807 (10)
H10A	0.4584	0.7481	0.7965	0.121*
H10B	0.3556	0.7462	0.8985	0.121*
H10C	0.3338	0.6921	0.7596	0.121*
C11	0.3930 (3)	0.3631 (3)	0.9603 (3)	0.0647 (8)
C12	0.3130 (4)	0.2610 (4)	1.0124 (5)	0.0943 (12)
H12A	0.3594	0.1870	1.0331	0.141*
H12B	0.2545	0.2393	0.9487	0.141*
H12C	0.2740	0.2914	1.0887	0.141*
H2	0.535 (4)	0.400 (3)	0.918 (5)	0.093 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0511 (4)	0.1127 (6)	0.0354 (3)	0.0220 (4)	−0.0027 (3)	−0.0153 (3)
O1	0.0387 (9)	0.148 (2)	0.0742 (16)	−0.0044 (12)	0.0069 (9)	−0.0040 (15)
O2	0.0664 (15)	0.107 (2)	0.094 (2)	0.0397 (15)	−0.0058 (14)	−0.0130 (17)
N1	0.0382 (9)	0.0674 (12)	0.0362 (9)	0.0040 (9)	0.0018 (7)	−0.0052 (9)
C1	0.0464 (13)	0.0745 (18)	0.077 (2)	0.0081 (13)	−0.0083 (13)	−0.0202 (17)
C2	0.0443 (13)	0.0829 (19)	0.088 (2)	0.0156 (15)	−0.0048 (14)	−0.0085 (18)
C3	0.0394 (13)	0.102 (2)	0.0618 (17)	−0.0053 (14)	−0.0092 (11)	0.0116 (17)
C4	0.0553 (14)	0.108 (2)	0.0496 (14)	−0.0198 (17)	−0.0045 (12)	−0.0076 (17)
C5	0.0478 (12)	0.0872 (18)	0.0428 (12)	−0.0064 (14)	0.0040 (10)	−0.0126 (14)
C6	0.0407 (11)	0.0578 (14)	0.0397 (11)	−0.0012 (10)	0.0003 (9)	0.0045 (11)
C7	0.0382 (11)	0.0586 (12)	0.0339 (10)	0.0024 (9)	−0.0003 (9)	0.0011 (10)
C8	0.0398 (11)	0.0725 (15)	0.0353 (10)	0.0058 (10)	−0.0005 (9)	−0.0058 (11)
C9	0.0440 (12)	0.101 (2)	0.0417 (12)	−0.0040 (14)	0.0006 (10)	−0.0012 (15)
C10	0.0640 (18)	0.096 (2)	0.082 (2)	−0.0207 (17)	0.0007 (17)	0.017 (2)
C11	0.0622 (16)	0.0814 (18)	0.0504 (15)	0.0225 (15)	−0.0073 (12)	−0.0103 (14)
C12	0.097 (3)	0.071 (2)	0.115 (3)	0.009 (2)	0.002 (3)	0.014 (2)

Geometric parameters (Å, º) top

S1—C7	1.662 (2)	C4—H4A	0.9300
O1—C9	1.279 (3)	C5—C6	1.393 (4)
O2—C11	1.268 (4)	C5—H5A	0.9300
O2—H2	0.858 (10)	C7—C8	1.494 (3)
N1—C7	1.337 (3)	C8—C11	1.400 (4)
N1—C6	1.419 (3)	C8—C9	1.413 (4)
N1—H1A	0.8600	C9—C10	1.488 (5)
C1—C6	1.372 (4)	C10—H10A	0.9600
C1—C2	1.397 (4)	C10—H10B	0.9600
C1—H1B	0.9300	C10—H10C	0.9600
C2—C3	1.363 (5)	C11—C12	1.501 (5)
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.382 (5)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C4—C5	1.361 (4)

C11—O2—H2	104 (3)	N1—C7—S1	126.13 (17)
C7—N1—C6	132.4 (2)	C8—C7—S1	120.92 (17)
C7—N1—H1A	113.8	C11—C8—C9	119.2 (2)
C6—N1—H1A	113.8	C11—C8—C7	120.9 (2)
C6—C1—C2	119.0 (3)	C9—C8—C7	119.9 (2)
C6—C1—H1B	120.5	O1—C9—C8	120.7 (3)
C2—C1—H1B	120.5	O1—C9—C10	116.9 (3)
C3—C2—C1	121.0 (3)	C8—C9—C10	122.4 (3)
C3—C2—H2A	119.5	C9—C10—H10A	109.5
C1—C2—H2A	119.5	C9—C10—H10B	109.5
C2—C3—C4	119.8 (3)	H10A—C10—H10B	109.5
C2—C3—H3A	120.1	C9—C10—H10C	109.5
C4—C3—H3A	120.1	H10A—C10—H10C	109.5
C5—C4—C3	119.6 (3)	H10B—C10—H10C	109.5
C5—C4—H4A	120.2	O2—C11—C8	121.9 (3)
C3—C4—H4A	120.2	O2—C11—C12	115.8 (3)
C4—C5—C6	121.2 (3)	C8—C11—C12	122.3 (3)
C4—C5—H5A	119.4	C11—C12—H12A	109.5
C6—C5—H5A	119.4	C11—C12—H12B	109.5
C1—C6—C5	119.3 (2)	H12A—C12—H12B	109.5
C1—C6—N1	125.0 (2)	C11—C12—H12C	109.5
C5—C6—N1	115.6 (2)	H12A—C12—H12C	109.5
N1—C7—C8	112.9 (2)	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.86	2.56	3.408 (2)	169
O2—H2···O1	0.86 (1)	1.66 (2)	2.468 (5)	156 (4)

Symmetry code: (i) −x+1/2, −y+1, z−1/2.

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(E)-2-Acetyl-3-hydr­oxy-N-phenyl­but-2-enethio­amide

Supporting information

Key indicators

checkCIF/PLATON results

(E)-2-Acetyl-3-hydroxy-N-phenylbut-2-enethioamide