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In the title mol­ecule, C11H12N2O3S, all bond lengths and angles are normal. Intra­molecular N—H...O and C—H...S hydrogen bonds influence the mol­ecular conformation. The crystal packing exhibits an extensive network formed by inter­molecular O—H...S, N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035088/cv2280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035088/cv2280Isup2.hkl
Contains datablock I

CCDC reference: 657829

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.107
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C9 .. 5.00 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 0 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

Comment top

The title compound, (I), is analogous to N-(4-Methylbenzoyl)-N'-(4-nitrophenyl)thiourea, (II) (Yusof et al., 2006), except that the 4-nitrophenyl group is replaced by amino-acetic acid group (Fig. 1). The molecule of (I) maintains its trans-cis configuration with respect to the position of the 4-methylbenzoyl and acetic acid groups relative to the thiono S1 atom across the C8—N1 and C9—N2 bonds, respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and are comparable to those in (II). The central thiourea, (S1/C9/N1/N2), phenyl ring (C1—C6) and amino-acetic acid (C10/C11/O2/O3/N2) fragments are essentially planar each with maximum deviation of 0.031 (2)° for atom C10 from the least square planes. The dihedral angles between the central thiourea and phenyl ring fragments is 8.23 (8)°. There are two intramolecular hydrogen bonds, N2—H2···O1 and C10—H10···S1 (Table 1), and as a result, a pseudo-six- and five-membered rings (O1···H2—N2—C9—N1—C8—O1 and H10B···S1—C9—N2—C10—H10B) are formed. The crystal packing exhibits extensive network formed by intermolecular O—H···S, N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For a related crystal structure, see: Yusof et al. (2006). For normal ranges of molecular bond lengths, see: Allen et al. (1987).

Experimental top

An equimolar amount of glycine (1.0 g, 0.01 mol) in 20 ml acetone was added dropwise into a stirring acetone solution (75 ml) containing 4-methylbenzoyl chloride (2.36 g, 0.01 mol) and ammonium thiocyanate (0.98 g, 0.01 mol). The solution mixture was refluxed for 6 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered and washed with distilled water and cold ethanol before dried under vacuum. Good quality crystals were obtained by recrystallization from methanol. Yield 77% (2.05 g). MP 375.2–376.4 K.

Refinement top

After their location in the difference map, all H-atoms were fixed geometrically at ideal positions (O—H, N—H and C—H of 0.82, 0.86 and 0.93–0.96 Å, respectively) and allowed to ride on the parent atoms with Uiso(H)= 1.2–1.5Ueq of the parent atom.

Structure description top

The title compound, (I), is analogous to N-(4-Methylbenzoyl)-N'-(4-nitrophenyl)thiourea, (II) (Yusof et al., 2006), except that the 4-nitrophenyl group is replaced by amino-acetic acid group (Fig. 1). The molecule of (I) maintains its trans-cis configuration with respect to the position of the 4-methylbenzoyl and acetic acid groups relative to the thiono S1 atom across the C8—N1 and C9—N2 bonds, respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and are comparable to those in (II). The central thiourea, (S1/C9/N1/N2), phenyl ring (C1—C6) and amino-acetic acid (C10/C11/O2/O3/N2) fragments are essentially planar each with maximum deviation of 0.031 (2)° for atom C10 from the least square planes. The dihedral angles between the central thiourea and phenyl ring fragments is 8.23 (8)°. There are two intramolecular hydrogen bonds, N2—H2···O1 and C10—H10···S1 (Table 1), and as a result, a pseudo-six- and five-membered rings (O1···H2—N2—C9—N1—C8—O1 and H10B···S1—C9—N2—C10—H10B) are formed. The crystal packing exhibits extensive network formed by intermolecular O—H···S, N—H···O and C—H···O hydrogen bonds (Table 1).

For a related crystal structure, see: Yusof et al. (2006). For normal ranges of molecular bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, (I), with the 50% probability displacement ellipsoids. The dashed line indicates intramolecular N—H···O and C—H···S hydrogen bonds.
N-[N-(4-Methylbenzoyl)carbamothioyl]glycine top
Crystal data top
C11H12N2O3SF(000) = 528
Mr = 252.29Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.664 (3) ÅCell parameters from 3055 reflections
b = 8.590 (2) Åθ = 1.9–26.0°
c = 12.962 (3) ŵ = 0.27 mm1
β = 113.917 (4)°T = 298 K
V = 1187.2 (5) Å3Block, colourless
Z = 40.50 × 0.48 × 0.21 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2322 independent reflections
Radiation source: fine-focus sealed tube2018 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 148
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1010
Tmin = 0.877, Tmax = 0.945l = 1515
6388 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.2581P]
where P = (Fo2 + 2Fc2)/3
2322 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C11H12N2O3SV = 1187.2 (5) Å3
Mr = 252.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.664 (3) ŵ = 0.27 mm1
b = 8.590 (2) ÅT = 298 K
c = 12.962 (3) Å0.50 × 0.48 × 0.21 mm
β = 113.917 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2322 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2018 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.945Rint = 0.017
6388 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.06Δρmax = 0.20 e Å3
2322 reflectionsΔρmin = 0.22 e Å3
156 parameters
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
xyzUiso*/Ueq
S10.01912 (5)0.77866 (6)1.17790 (4)0.05108 (18)
O10.23600 (14)0.50912 (19)1.01638 (11)0.0661 (4)
O20.29873 (13)0.54526 (17)1.48607 (9)0.0601 (4)
H2A0.35270.59971.53280.090*
O30.34152 (12)0.69059 (14)1.36404 (10)0.0477 (3)
N10.08679 (13)0.67815 (16)1.01690 (11)0.0402 (3)
H1A0.03100.74320.97560.048*
N20.16263 (13)0.53866 (15)1.18306 (10)0.0399 (3)
H2B0.20010.48201.15150.048*
C10.17221 (17)0.5590 (2)0.78550 (15)0.0505 (4)
H10.21810.46990.81780.061*
C20.14413 (19)0.5940 (2)0.67371 (16)0.0564 (5)
H20.17230.52810.63200.068*
C30.07530 (18)0.7243 (2)0.62259 (15)0.0492 (4)
C40.03829 (19)0.8234 (2)0.68810 (15)0.0501 (4)
H40.00630.91340.65600.060*
C50.06646 (17)0.79070 (19)0.79981 (14)0.0441 (4)
H50.04130.85910.84230.053*
C60.13205 (15)0.6564 (2)0.84968 (13)0.0405 (4)
C70.0398 (3)0.7588 (3)0.49940 (18)0.0707 (6)
H7A0.10370.82160.49140.106*
H7B0.03860.81370.46940.106*
H7C0.03160.66280.45900.106*
C80.15811 (15)0.6075 (2)0.96716 (14)0.0426 (4)
C90.09453 (15)0.65652 (18)1.12535 (13)0.0369 (4)
C100.17812 (16)0.49900 (18)1.29587 (13)0.0399 (4)
H10A0.19660.38881.30830.048*
H10B0.10020.51871.30370.048*
C110.28158 (15)0.59043 (18)1.38379 (12)0.0371 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0641 (3)0.0556 (3)0.0328 (2)0.0194 (2)0.0189 (2)0.00378 (18)
O10.0655 (8)0.0874 (10)0.0461 (7)0.0351 (8)0.0232 (7)0.0126 (7)
O20.0708 (9)0.0704 (9)0.0297 (6)0.0245 (7)0.0105 (6)0.0026 (6)
O30.0497 (7)0.0497 (7)0.0377 (6)0.0116 (6)0.0117 (5)0.0022 (5)
N10.0445 (8)0.0444 (7)0.0285 (6)0.0070 (6)0.0117 (6)0.0026 (6)
N20.0455 (8)0.0389 (7)0.0300 (7)0.0043 (6)0.0098 (6)0.0009 (5)
C10.0518 (11)0.0563 (10)0.0470 (10)0.0065 (8)0.0238 (8)0.0004 (8)
C20.0664 (12)0.0646 (12)0.0499 (10)0.0028 (10)0.0355 (10)0.0094 (9)
C30.0551 (11)0.0573 (11)0.0389 (9)0.0155 (9)0.0227 (8)0.0042 (8)
C40.0576 (11)0.0488 (10)0.0458 (10)0.0041 (8)0.0230 (9)0.0053 (8)
C50.0515 (10)0.0435 (9)0.0411 (9)0.0051 (7)0.0227 (8)0.0039 (7)
C60.0369 (8)0.0485 (9)0.0349 (8)0.0053 (7)0.0132 (7)0.0030 (7)
C70.0918 (17)0.0805 (15)0.0445 (11)0.0150 (13)0.0325 (12)0.0004 (10)
C80.0386 (9)0.0497 (9)0.0368 (9)0.0018 (7)0.0125 (7)0.0024 (7)
C90.0380 (8)0.0381 (8)0.0293 (7)0.0035 (7)0.0081 (6)0.0025 (6)
C100.0447 (9)0.0377 (8)0.0318 (8)0.0024 (7)0.0100 (7)0.0030 (6)
C110.0396 (8)0.0369 (8)0.0314 (8)0.0033 (7)0.0109 (7)0.0029 (6)
Geometric parameters (Å, º) top
S1—C91.6806 (17)C2—H20.9300
O1—C81.215 (2)C3—C41.389 (3)
O2—C111.3164 (19)C3—C71.507 (3)
O2—H2A0.8200C4—C51.378 (2)
O3—C111.200 (2)C4—H40.9300
N1—C81.382 (2)C5—C61.390 (2)
N1—C91.384 (2)C5—H50.9300
N1—H1A0.8600C6—C81.488 (2)
N2—C91.317 (2)C7—H7A0.9600
N2—C101.440 (2)C7—H7B0.9600
N2—H2B0.8600C7—H7C0.9600
C1—C21.383 (3)C10—C111.502 (2)
C1—C61.389 (2)C10—H10A0.9700
C1—H10.9300C10—H10B0.9700
C2—C31.381 (3)
C11—O2—H2A109.5C1—C6—C8117.67 (16)
C8—N1—C9127.66 (14)C5—C6—C8123.78 (15)
C8—N1—H1A116.2C3—C7—H7A109.5
C9—N1—H1A116.2C3—C7—H7B109.5
C9—N2—C10123.87 (14)H7A—C7—H7B109.5
C9—N2—H2B118.1C3—C7—H7C109.5
C10—N2—H2B118.1H7A—C7—H7C109.5
C2—C1—C6120.17 (18)H7B—C7—H7C109.5
C2—C1—H1119.9O1—C8—N1121.58 (15)
C6—C1—H1119.9O1—C8—C6122.21 (15)
C3—C2—C1121.59 (17)N1—C8—C6116.20 (14)
C3—C2—H2119.2N2—C9—N1117.14 (14)
C1—C2—H2119.2N2—C9—S1122.96 (12)
C2—C3—C4117.90 (17)N1—C9—S1119.90 (12)
C2—C3—C7121.61 (18)N2—C10—C11112.22 (13)
C4—C3—C7120.49 (19)N2—C10—H10A109.2
C5—C4—C3121.12 (18)C11—C10—H10A109.2
C5—C4—H4119.4N2—C10—H10B109.2
C3—C4—H4119.4C11—C10—H10B109.2
C4—C5—C6120.65 (16)H10A—C10—H10B107.9
C4—C5—H5119.7O3—C11—O2124.22 (15)
C6—C5—H5119.7O3—C11—C10124.84 (14)
C1—C6—C5118.52 (16)O2—C11—C10110.93 (14)
C6—C1—C2—C30.6 (3)C1—C6—C8—O117.6 (3)
C1—C2—C3—C42.2 (3)C5—C6—C8—O1164.65 (18)
C1—C2—C3—C7177.24 (19)C1—C6—C8—N1161.14 (16)
C2—C3—C4—C51.7 (3)C5—C6—C8—N116.6 (2)
C7—C3—C4—C5177.80 (18)C10—N2—C9—N1178.83 (14)
C3—C4—C5—C60.5 (3)C10—N2—C9—S11.4 (2)
C2—C1—C6—C51.7 (3)C8—N1—C9—N211.8 (2)
C2—C1—C6—C8176.21 (16)C8—N1—C9—S1168.04 (14)
C4—C5—C6—C12.2 (3)C9—N2—C10—C1184.95 (19)
C4—C5—C6—C8175.53 (16)N2—C10—C11—O33.3 (2)
C9—N1—C8—O13.0 (3)N2—C10—C11—O2176.19 (14)
C9—N1—C8—C6178.23 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.861.972.639 (2)133
C10—H10B···S10.972.703.0413 (19)101
O2—H2A···S1i0.822.333.1458 (16)172
N1—H1A···O3ii0.862.172.964 (2)153
N2—H2B···O3iii0.862.543.0481 (19)119
C5—H5···O3ii0.932.493.062 (3)119
C7—H7A···O1iv0.962.503.455 (4)173
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y1/2, z+5/2; (iv) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC11H12N2O3S
Mr252.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.664 (3), 8.590 (2), 12.962 (3)
β (°) 113.917 (4)
V3)1187.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.50 × 0.48 × 0.21
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.877, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections
6388, 2322, 2018
Rint0.017
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 1.06
No. of reflections2322
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.861.972.639 (2)133
C10—H10B···S10.972.703.0413 (19)101
O2—H2A···S1i0.822.333.1458 (16)172
N1—H1A···O3ii0.862.172.964 (2)153
N2—H2B···O3iii0.862.543.0481 (19)119
C7—H7A···O1iv0.962.503.455 (4)173
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y1/2, z+5/2; (iv) x+1/2, y+1/2, z+3/2.
 

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