2-(3-Benzoyl­thio­ureido)ethanoic acid dimeth­yl sulfoxide solvate

In the title compound, C₁₀H₁₀N₂O₃S·C₂H₆SO, the ethanoic acid fragment and benzene ring make dihedral angles of 3.61 (9) and 20.77 (9)°, respectively, with the central thio­urea N₂CS group. In the crystal structure, an inter­molecular O—H...O hydrogen bond exists between the hydr­oxy group of the ethanoic acid fragment and the O atom of the dimeth­yl sulfoxide solvent mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.077
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S2

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           25.99
           From the CIF: _reflns_number_total               2725
           Count of symmetry unique reflns         1620
           Completeness (_total/calc)            168.21%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1105
           Fraction of Friedel pairs measured     0.682
           Are heavy atom types Z>Si present        yes

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

   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(3-Benzoylthioureido)ethanoic acid dimethyl sulfoxide solvate

Crystal data

C10H10N2O3S·C2H6OS	F(000) = 332
Mr = 316.39	Dx = 1.412 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 734 reflections
a = 10.074 (2) Å	θ = 1.6–26.0°
b = 5.6289 (12) Å	µ = 0.37 mm^−1
c = 13.969 (3) Å	T = 298 K
β = 110.074 (4)°	Block, yellow
V = 744.0 (3) Å^3	0.44 × 0.34 × 0.17 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.854, Tmax = 0.940	l = −15→17
4157 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 0.1167P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2725 reflections	Δρmax = 0.19 e Å^−3
184 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1117 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (7)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.14142 (6)	0.94424 (12)	0.92765 (5)	0.05230 (17)
S2	0.67896 (7)	1.04731 (12)	0.45849 (5)	0.05832 (19)
O1	0.13275 (16)	1.0048 (3)	0.73050 (12)	0.0572 (5)
O2	−0.10726 (17)	1.5328 (4)	0.65101 (13)	0.0624 (5)
O3	−0.3078 (2)	1.6498 (4)	0.67026 (15)	0.0645 (5)
H3A	−0.3016	1.7618	0.6345	0.097*
O4	0.66629 (19)	1.0260 (4)	0.56209 (13)	0.0652 (5)
N1	0.07001 (19)	0.8614 (4)	0.86172 (14)	0.0460 (5)
H1A	0.0931	0.7594	0.9105	0.055*
N2	−0.07524 (19)	1.1742 (4)	0.78547 (14)	0.0477 (5)
H2A	−0.0216	1.1921	0.7496	0.057*
C1	0.2733 (2)	0.4817 (4)	0.87876 (16)	0.0475 (6)
H1	0.1942	0.4373	0.8943	0.057*
C2	0.3903 (3)	0.3343 (5)	0.90534 (18)	0.0559 (6)
H2	0.3903	0.1920	0.9391	0.067*
C3	0.5071 (3)	0.4003 (5)	0.88129 (18)	0.0565 (7)
H3	0.5862	0.3023	0.8995	0.068*
C4	0.5075 (3)	0.6076 (5)	0.8312 (2)	0.0569 (7)
H4	0.5864	0.6498	0.8148	0.068*
C5	0.3913 (2)	0.7550 (5)	0.80467 (19)	0.0500 (6)
H5	0.3918	0.8960	0.7701	0.060*
C6	0.2731 (2)	0.6935 (4)	0.82944 (16)	0.0418 (5)
C7	0.1531 (2)	0.8658 (4)	0.80102 (17)	0.0437 (5)
C8	−0.0466 (2)	1.0028 (4)	0.85308 (15)	0.0422 (5)
C9	−0.1931 (2)	1.3342 (5)	0.76879 (18)	0.0502 (6)
H9A	−0.1851	1.4132	0.8322	0.060*
H9B	−0.2806	1.2443	0.7468	0.060*
C10	−0.1970 (2)	1.5164 (5)	0.68969 (16)	0.0471 (5)
C11	0.8625 (3)	1.0575 (8)	0.4808 (2)	0.0904 (10)
H11A	0.9002	1.2056	0.5127	0.136*
H11B	0.8787	1.0438	0.4172	0.136*
H11C	0.9084	0.9285	0.5247	0.136*
C12	0.6429 (4)	0.7620 (6)	0.4031 (3)	0.0857 (10)
H12A	0.7131	0.6520	0.4428	0.129*
H12B	0.6449	0.7677	0.3349	0.129*
H12C	0.5512	0.7111	0.4014	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0525 (3)	0.0592 (4)	0.0565 (3)	0.0025 (3)	0.0333 (3)	0.0009 (3)
S2	0.0678 (4)	0.0554 (4)	0.0549 (3)	0.0102 (3)	0.0251 (3)	0.0081 (3)
O1	0.0560 (9)	0.0661 (13)	0.0605 (10)	0.0169 (9)	0.0340 (8)	0.0176 (9)
O2	0.0594 (10)	0.0648 (12)	0.0763 (11)	0.0098 (9)	0.0405 (9)	0.0125 (10)
O3	0.0651 (11)	0.0713 (13)	0.0686 (12)	0.0245 (10)	0.0376 (10)	0.0214 (10)
O4	0.0806 (12)	0.0623 (12)	0.0622 (10)	0.0140 (11)	0.0367 (9)	0.0049 (10)
N1	0.0473 (11)	0.0540 (12)	0.0432 (10)	0.0108 (9)	0.0237 (9)	0.0063 (9)
N2	0.0431 (10)	0.0562 (12)	0.0511 (11)	0.0086 (9)	0.0258 (9)	0.0050 (10)
C1	0.0548 (13)	0.0493 (16)	0.0468 (12)	0.0014 (11)	0.0283 (10)	−0.0006 (11)
C2	0.0748 (18)	0.0483 (15)	0.0482 (13)	0.0110 (13)	0.0259 (13)	0.0044 (12)
C3	0.0506 (14)	0.0632 (19)	0.0548 (15)	0.0172 (13)	0.0170 (12)	−0.0045 (13)
C4	0.0431 (13)	0.0664 (19)	0.0676 (16)	0.0035 (12)	0.0273 (12)	−0.0076 (13)
C5	0.0543 (14)	0.0512 (15)	0.0542 (14)	0.0021 (11)	0.0314 (12)	−0.0010 (11)
C6	0.0419 (11)	0.0476 (13)	0.0401 (11)	0.0031 (10)	0.0195 (9)	−0.0053 (10)
C7	0.0423 (12)	0.0493 (14)	0.0437 (12)	0.0013 (10)	0.0203 (10)	0.0000 (10)
C8	0.0398 (11)	0.0497 (16)	0.0392 (10)	−0.0015 (10)	0.0161 (9)	−0.0076 (10)
C9	0.0464 (13)	0.0568 (15)	0.0536 (14)	0.0097 (11)	0.0253 (11)	0.0027 (12)
C10	0.0458 (12)	0.0502 (14)	0.0477 (12)	0.0030 (11)	0.0192 (10)	−0.0011 (11)
C11	0.082 (2)	0.112 (3)	0.093 (2)	−0.014 (2)	0.0507 (18)	−0.009 (2)
C12	0.107 (3)	0.082 (3)	0.0675 (19)	−0.010 (2)	0.0296 (18)	−0.0158 (17)

Geometric parameters (Å, º)

S1—C8	1.670 (2)	C2—H2	0.9300
S2—O4	1.5007 (19)	C3—C4	1.361 (4)
S2—C12	1.765 (3)	C3—H3	0.9300
S2—C11	1.767 (3)	C4—C5	1.378 (3)
O1—C7	1.219 (3)	C4—H4	0.9300
O2—C10	1.206 (3)	C5—C6	1.393 (3)
O3—C10	1.294 (3)	C5—H5	0.9300
O3—H3A	0.8200	C6—C7	1.493 (3)
N1—C7	1.381 (3)	C9—C10	1.498 (3)
N1—C8	1.389 (3)	C9—H9A	0.9700
N1—H1A	0.8600	C9—H9B	0.9700
N2—C8	1.311 (3)	C11—H11A	0.9600
N2—C9	1.444 (3)	C11—H11B	0.9600
N2—H2A	0.8600	C11—H11C	0.9600
C1—C6	1.377 (3)	C12—H12A	0.9600
C1—C2	1.384 (3)	C12—H12B	0.9600
C1—H1	0.9300	C12—H12C	0.9600
C2—C3	1.380 (4)
O4—S2—C12	106.10 (15)	O1—C7—N1	122.6 (2)
O4—S2—C11	105.22 (13)	O1—C7—C6	121.87 (19)
C12—S2—C11	98.74 (19)	N1—C7—C6	115.5 (2)
C10—O3—H3A	109.5	N2—C8—N1	117.03 (19)
C7—N1—C8	127.5 (2)	N2—C8—S1	124.27 (17)
C7—N1—H1A	116.2	N1—C8—S1	118.70 (17)
C8—N1—H1A	116.2	N2—C9—C10	110.97 (18)
C8—N2—C9	122.71 (19)	N2—C9—H9A	109.4
C8—N2—H2A	118.6	C10—C9—H9A	109.4
C9—N2—H2A	118.6	N2—C9—H9B	109.4
C6—C1—C2	120.5 (2)	C10—C9—H9B	109.4
C6—C1—H1	119.7	H9A—C9—H9B	108.0
C2—C1—H1	119.7	O2—C10—O3	125.9 (2)
C3—C2—C1	119.5 (3)	O2—C10—C9	123.3 (2)
C3—C2—H2	120.3	O3—C10—C9	110.75 (19)
C1—C2—H2	120.3	S2—C11—H11A	109.5
C4—C3—C2	120.6 (2)	S2—C11—H11B	109.5
C4—C3—H3	119.7	H11A—C11—H11B	109.5
C2—C3—H3	119.7	S2—C11—H11C	109.5
C3—C4—C5	120.2 (2)	H11A—C11—H11C	109.5
C3—C4—H4	119.9	H11B—C11—H11C	109.5
C5—C4—H4	119.9	S2—C12—H12A	109.5
C4—C5—C6	120.2 (2)	S2—C12—H12B	109.5
C4—C5—H5	119.9	H12A—C12—H12B	109.5
C6—C5—H5	119.9	S2—C12—H12C	109.5
C1—C6—C5	119.0 (2)	H12A—C12—H12C	109.5
C1—C6—C7	123.9 (2)	H12B—C12—H12C	109.5
C5—C6—C7	117.1 (2)
C6—C1—C2—C3	−0.5 (3)	C5—C6—C7—O1	26.0 (3)
C1—C2—C3—C4	−0.5 (4)	C1—C6—C7—N1	27.2 (3)
C2—C3—C4—C5	0.5 (4)	C5—C6—C7—N1	−152.2 (2)
C3—C4—C5—C6	0.4 (4)	C9—N2—C8—N1	−179.9 (2)
C2—C1—C6—C5	1.4 (3)	C9—N2—C8—S1	0.6 (3)
C2—C1—C6—C7	−178.0 (2)	C7—N1—C8—N2	−6.3 (3)
C4—C5—C6—C1	−1.3 (4)	C7—N1—C8—S1	173.25 (19)
C4—C5—C6—C7	178.2 (2)	C8—N2—C9—C10	178.1 (2)
C8—N1—C7—O1	1.2 (4)	N2—C9—C10—O2	−4.4 (4)
C8—N1—C7—C6	179.4 (2)	N2—C9—C10—O3	175.9 (2)
C1—C6—C7—O1	−154.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.97	2.645 (3)	134
N2—H2A···O2	0.86	2.35	2.700 (3)	105
N1—H1A···S1^i	0.86	2.78	3.638 (2)	174
O3—H3A···O4^ii	0.82	1.76	2.562 (3)	164
C1—H1···S1^i	0.93	2.72	3.404 (2)	132
C4—H4···O3^iii	0.93	2.59	3.383 (4)	144

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