




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809046169/ci2952sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809046169/ci2952Isup2.hkl |
CCDC reference: 758286
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.089
- wR factor = 0.172
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 6
Alert level G PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c .... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized according to a previously reported method (Hassan et al., 2008a). Yellowish crystals, suitable for X-ray analysis, were obtained by slow evaporation of a CH2Cl2 solution at room temperature (yield 73%).
H atoms were positioned geometrically [N-H = 0.86 Å and C-H = 0.93-0.97 Å] and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq (C,N) and 1.5Ueq(Cmethyl).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
C11H12N2O3S | F(000) = 528 |
Mr = 252.29 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 871 reflections |
a = 14.5804 (15) Å | θ = 1.8–25.5° |
b = 4.9740 (5) Å | µ = 0.26 mm−1 |
c = 16.9133 (16) Å | T = 298 K |
β = 96.210 (2)° | Needle, colourless |
V = 1219.4 (2) Å3 | 0.48 × 0.14 × 0.06 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2264 independent reflections |
Radiation source: fine-focus sealed tube | 1600 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −17→17 |
Tmin = 0.884, Tmax = 0.984 | k = −5→6 |
6881 measured reflections | l = −17→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.089 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.24 | w = 1/[σ2(Fo2) + (0.0474P)2 + 0.746P] where P = (Fo2 + 2Fc2)/3 |
2264 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C11H12N2O3S | V = 1219.4 (2) Å3 |
Mr = 252.29 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.5804 (15) Å | µ = 0.26 mm−1 |
b = 4.9740 (5) Å | T = 298 K |
c = 16.9133 (16) Å | 0.48 × 0.14 × 0.06 mm |
β = 96.210 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 2264 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1600 reflections with I > 2σ(I) |
Tmin = 0.884, Tmax = 0.984 | Rint = 0.048 |
6881 measured reflections |
R[F2 > 2σ(F2)] = 0.089 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.24 | Δρmax = 0.26 e Å−3 |
2264 reflections | Δρmin = −0.18 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.50901 (8) | 0.0880 (3) | 0.62465 (7) | 0.0818 (5) | |
O1 | 0.2035 (2) | 0.1002 (7) | 0.53998 (17) | 0.0725 (10) | |
N1 | 0.3541 (2) | −0.0034 (7) | 0.53458 (18) | 0.0545 (9) | |
H1A | 0.3909 | −0.0822 | 0.5055 | 0.065* | |
C9 | 0.3780 (3) | 0.4046 (9) | 0.7161 (2) | 0.0610 (12) | |
H9A | 0.3380 | 0.5543 | 0.7257 | 0.073* | |
H9B | 0.4388 | 0.4763 | 0.7105 | 0.073* | |
C6 | 0.2391 (3) | −0.2034 (9) | 0.4391 (2) | 0.0494 (10) | |
N2 | 0.3429 (2) | 0.2733 (8) | 0.64340 (18) | 0.0576 (10) | |
H2A | 0.2854 | 0.2906 | 0.6265 | 0.069* | |
O3 | 0.4423 (2) | 0.3093 (7) | 0.84511 (17) | 0.0740 (10) | |
C7 | 0.2621 (3) | −0.0237 (9) | 0.5083 (2) | 0.0535 (11) | |
C1 | 0.2954 (3) | −0.4110 (9) | 0.4191 (2) | 0.0555 (11) | |
H1B | 0.3509 | −0.4435 | 0.4501 | 0.067* | |
O2 | 0.3394 (2) | 0.0172 (7) | 0.7891 (2) | 0.0812 (10) | |
C10 | 0.3840 (3) | 0.2182 (10) | 0.7862 (2) | 0.0553 (11) | |
C8 | 0.3961 (3) | 0.1265 (9) | 0.6015 (2) | 0.0542 (11) | |
C5 | 0.1559 (3) | −0.1619 (9) | 0.3927 (2) | 0.0602 (12) | |
H5A | 0.1168 | −0.0250 | 0.4056 | 0.072* | |
C4 | 0.1308 (3) | −0.3236 (10) | 0.3269 (3) | 0.0654 (13) | |
H4A | 0.0753 | −0.2938 | 0.2956 | 0.078* | |
C3 | 0.1877 (4) | −0.5258 (11) | 0.3085 (3) | 0.0704 (14) | |
H3A | 0.1707 | −0.6352 | 0.2647 | 0.084* | |
C2 | 0.2700 (3) | −0.5688 (10) | 0.3542 (3) | 0.0640 (13) | |
H2B | 0.3088 | −0.7062 | 0.3409 | 0.077* | |
C11 | 0.4497 (4) | 0.1530 (13) | 0.9180 (3) | 0.0918 (19) | |
H11A | 0.4937 | 0.2362 | 0.9568 | 0.138* | |
H11B | 0.4698 | −0.0259 | 0.9074 | 0.138* | |
H11C | 0.3906 | 0.1454 | 0.9381 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0492 (7) | 0.1335 (14) | 0.0612 (8) | 0.0052 (8) | −0.0012 (5) | −0.0188 (8) |
O1 | 0.0499 (18) | 0.093 (3) | 0.075 (2) | 0.0001 (17) | 0.0082 (15) | −0.0248 (19) |
N1 | 0.0436 (19) | 0.070 (3) | 0.049 (2) | 0.0069 (17) | 0.0017 (15) | −0.0076 (18) |
C9 | 0.065 (3) | 0.059 (3) | 0.058 (3) | −0.006 (2) | 0.006 (2) | −0.009 (2) |
C6 | 0.049 (2) | 0.055 (3) | 0.045 (2) | −0.014 (2) | 0.0068 (19) | 0.003 (2) |
N2 | 0.052 (2) | 0.066 (3) | 0.054 (2) | 0.0030 (19) | −0.0007 (17) | −0.0090 (19) |
O3 | 0.073 (2) | 0.095 (3) | 0.0531 (18) | −0.0153 (19) | 0.0021 (15) | −0.0035 (18) |
C7 | 0.048 (2) | 0.058 (3) | 0.055 (3) | −0.002 (2) | 0.008 (2) | 0.002 (2) |
C1 | 0.062 (3) | 0.051 (3) | 0.054 (3) | −0.004 (2) | 0.005 (2) | 0.001 (2) |
O2 | 0.092 (2) | 0.065 (2) | 0.086 (2) | −0.017 (2) | 0.0060 (18) | 0.0004 (19) |
C10 | 0.051 (3) | 0.056 (3) | 0.060 (3) | 0.001 (2) | 0.014 (2) | −0.009 (2) |
C8 | 0.054 (3) | 0.062 (3) | 0.045 (2) | −0.001 (2) | 0.0012 (19) | 0.001 (2) |
C5 | 0.058 (3) | 0.060 (3) | 0.063 (3) | −0.007 (2) | 0.008 (2) | −0.003 (2) |
C4 | 0.059 (3) | 0.075 (4) | 0.059 (3) | −0.016 (3) | −0.006 (2) | 0.006 (3) |
C3 | 0.093 (4) | 0.063 (3) | 0.054 (3) | −0.018 (3) | 0.005 (3) | −0.004 (3) |
C2 | 0.080 (3) | 0.051 (3) | 0.062 (3) | 0.000 (2) | 0.011 (2) | −0.005 (2) |
C11 | 0.098 (4) | 0.123 (5) | 0.055 (3) | 0.017 (4) | 0.008 (3) | 0.011 (3) |
S1—C8 | 1.661 (4) | O3—C11 | 1.452 (5) |
O1—C7 | 1.223 (5) | C1—C2 | 1.368 (6) |
N1—C7 | 1.371 (5) | C1—H1B | 0.93 |
N1—C8 | 1.387 (5) | O2—C10 | 1.197 (5) |
N1—H1A | 0.86 | C5—C4 | 1.389 (6) |
C9—N2 | 1.437 (5) | C5—H5A | 0.93 |
C9—C10 | 1.499 (6) | C4—C3 | 1.361 (6) |
C9—H9A | 0.97 | C4—H4A | 0.93 |
C9—H9B | 0.97 | C3—C2 | 1.372 (6) |
C6—C1 | 1.384 (6) | C3—H3A | 0.93 |
C6—C5 | 1.386 (5) | C2—H2B | 0.93 |
C6—C7 | 1.482 (6) | C11—H11A | 0.96 |
N2—C8 | 1.326 (5) | C11—H11B | 0.96 |
N2—H2A | 0.86 | C11—H11C | 0.96 |
O3—C10 | 1.318 (5) | ||
C7—N1—C8 | 129.0 (3) | O2—C10—C9 | 124.3 (4) |
C7—N1—H1A | 115.5 | O3—C10—C9 | 111.3 (4) |
C8—N1—H1A | 115.5 | N2—C8—N1 | 117.4 (4) |
N2—C9—C10 | 112.4 (4) | N2—C8—S1 | 124.0 (3) |
N2—C9—H9A | 109.1 | N1—C8—S1 | 118.6 (3) |
C10—C9—H9A | 109.1 | C6—C5—C4 | 120.4 (4) |
N2—C9—H9B | 109.1 | C6—C5—H5A | 119.8 |
C10—C9—H9B | 109.1 | C4—C5—H5A | 119.8 |
H9A—C9—H9B | 107.9 | C3—C4—C5 | 119.8 (4) |
C1—C6—C5 | 118.6 (4) | C3—C4—H4A | 120.1 |
C1—C6—C7 | 123.6 (4) | C5—C4—H4A | 120.1 |
C5—C6—C7 | 117.9 (4) | C4—C3—C2 | 120.2 (5) |
C8—N2—C9 | 122.3 (4) | C4—C3—H3A | 119.9 |
C8—N2—H2A | 118.9 | C2—C3—H3A | 119.9 |
C9—N2—H2A | 118.9 | C1—C2—C3 | 120.5 (5) |
C10—O3—C11 | 116.2 (4) | C1—C2—H2B | 119.8 |
O1—C7—N1 | 121.8 (4) | C3—C2—H2B | 119.8 |
O1—C7—C6 | 122.7 (4) | O3—C11—H11A | 109.5 |
N1—C7—C6 | 115.5 (4) | O3—C11—H11B | 109.5 |
C2—C1—C6 | 120.5 (4) | H11A—C11—H11B | 109.5 |
C2—C1—H1B | 119.7 | O3—C11—H11C | 109.5 |
C6—C1—H1B | 119.7 | H11A—C11—H11C | 109.5 |
O2—C10—O3 | 124.4 (4) | H11B—C11—H11C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.02 | 2.676 (4) | 132 |
C9—H9B···S1 | 0.97 | 2.68 | 3.027 (4) | 101 |
N1—H1A···S1i | 0.86 | 2.77 | 3.547 (3) | 151 |
C9—H9A···O2ii | 0.97 | 2.54 | 3.358 (6) | 142 |
C9—H9A···O2iii | 0.97 | 2.58 | 3.211 (5) | 123 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C11H12N2O3S |
Mr | 252.29 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 14.5804 (15), 4.9740 (5), 16.9133 (16) |
β (°) | 96.210 (2) |
V (Å3) | 1219.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.48 × 0.14 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.884, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6881, 2264, 1600 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.089, 0.172, 1.24 |
No. of reflections | 2264 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.18 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.02 | 2.676 (4) | 132 |
N1—H1A···S1i | 0.86 | 2.77 | 3.547 (3) | 151 |
C9—H9A···O2ii | 0.97 | 2.54 | 3.358 (6) | 142 |
C9—H9A···O2iii | 0.97 | 2.58 | 3.211 (5) | 123 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) −x+1/2, y+1/2, −z+3/2. |
The title compound, (I), is a methyl ester derivative of glycine thiourea analogous to our previously reported ethyl-2-(3-benzoylthioureido)acetate (II) (Hassan et al., 2008a), propyl-2-(3-benzoylthioureido)acetate (III) (Hassan et al., 2008b) and butyl-2-(3-benzoylthioureido)acetate (IV) (Hassan et al., 2008c). The methyl acetate fragment and the benzoyl group adopt a cis-trans configuration, respectively, with respect to the thiono S atom across the C—N bonds (Fig 1). The dihedral angle between the phenyl ring (C1–C6) and the central fragment (S1/N1/N2/C8/C9) is 20.12 (19)°. The bond lengths (Allen et al., 1987) and angles in the molecule are in normal ranges and comparable to those of (II), (III) and (IV). The methyl acetate group (O2/O3/C9/C10/C11) is planar, with a maximum deviation of 0.023 (3) Å for atom O3. The dihedral angle between the phenyl ring and the methyl acetate group is 73.4 (2)°. An intramolecular N2—H2A···O1 hydrogen bond (Table 1) forms a pseudo-five-membered N2/H2A/O1/C7/N1/C8 ring.
Intermolecular N1—H1A···S1 and C9—H9A···O2 hydrogen bonds (Table 1) link the molecules into a two-dimensional network parallel to the (101) (Fig 2).