Download citation
Download citation
link to html
In the title compound, C8H10N2OS, the dihedral angle between the benzene ring and the thio­urea group is 59.23 (4)°. Mol­ecules are linked via N—H...O/S hydrogen bonds, forming a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038566/ob2070sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038566/ob2070Isup2.hkl
Contains datablock I

CCDC reference: 624954

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.083
  • Data-to-parameter ratio = 20.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C8 .. 5.58 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun and I.A. Razak are supervisors of Jeannie B.-J. Teh whereas S.M. Dharmaprakash is the supervisor of Mari Sithambaram Karthikeyan, Bantwal Shivarama and P.S. Patil in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); 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).

N-(4-Methoxyphenyl)thiourea top
Crystal data top
C8H10N2OSZ = 2
Mr = 182.24F(000) = 192
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7328 (2) ÅCell parameters from 6119 reflections
b = 8.3813 (2) Åθ = 2.6–30.0°
c = 9.0571 (2) ŵ = 0.32 mm1
α = 63.779 (1)°T = 100 K
β = 72.413 (1)°Block, black
γ = 83.428 (1)°0.51 × 0.43 × 0.29 mm
V = 436.96 (2) Å3
Data collection top
Brucker SMART APEX2 CCD
diffractometer
2531 independent reflections
Radiation source: fine-focus sealed tube2432 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.6°
ω scansh = 89
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1111
Tmin = 0.853, Tmax = 0.913l = 1212
4876 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.1605P]
where P = (Fo2 + 2Fc2)/3
2531 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.35 e Å3
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
S11.03388 (4)0.22141 (3)0.54932 (3)0.01413 (8)
O10.39369 (11)0.84909 (10)0.12690 (9)0.01608 (15)
N10.83759 (14)0.48002 (11)0.35198 (11)0.01420 (16)
N20.85042 (14)0.21414 (11)0.33120 (11)0.01551 (17)
C10.70653 (15)0.82462 (13)0.03598 (12)0.01485 (18)
H1A0.76510.92890.13040.018*
C20.81435 (15)0.72727 (13)0.08457 (13)0.01501 (18)
H2A0.94630.76580.06930.018*
C30.72618 (15)0.57281 (12)0.22756 (12)0.01257 (17)
C40.52703 (15)0.51556 (13)0.25123 (12)0.01478 (18)
H4A0.46620.41400.34820.018*
C50.42008 (15)0.60994 (13)0.13037 (13)0.01515 (18)
H5A0.28870.57060.14520.018*
C60.50999 (15)0.76453 (12)0.01401 (12)0.01300 (17)
C70.49334 (17)0.99992 (14)0.28097 (13)0.01800 (19)
H7A0.40091.04870.35220.027*
H7B0.61880.96320.34190.027*
H7C0.52681.08860.25180.027*
C80.89783 (14)0.31099 (12)0.40008 (12)0.01178 (17)
H1B0.882 (3)0.544 (2)0.391 (2)0.029 (4)*
H2B0.786 (3)0.256 (2)0.253 (2)0.026 (4)*
H2C0.892 (3)0.103 (2)0.365 (2)0.023 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01846 (13)0.00991 (12)0.01816 (13)0.00165 (8)0.01189 (9)0.00562 (9)
O10.0164 (3)0.0158 (3)0.0157 (3)0.0002 (2)0.0099 (3)0.0029 (3)
N10.0199 (4)0.0106 (3)0.0169 (4)0.0027 (3)0.0120 (3)0.0063 (3)
N20.0222 (4)0.0121 (4)0.0184 (4)0.0038 (3)0.0129 (3)0.0082 (3)
C10.0150 (4)0.0139 (4)0.0145 (4)0.0008 (3)0.0064 (3)0.0034 (3)
C20.0142 (4)0.0142 (4)0.0173 (4)0.0002 (3)0.0078 (3)0.0051 (3)
C30.0153 (4)0.0113 (4)0.0141 (4)0.0027 (3)0.0077 (3)0.0063 (3)
C40.0157 (4)0.0126 (4)0.0150 (4)0.0000 (3)0.0058 (3)0.0040 (3)
C50.0135 (4)0.0148 (4)0.0172 (4)0.0004 (3)0.0067 (3)0.0052 (3)
C60.0140 (4)0.0138 (4)0.0135 (4)0.0024 (3)0.0073 (3)0.0063 (3)
C70.0211 (5)0.0169 (4)0.0150 (4)0.0003 (4)0.0095 (4)0.0031 (4)
C80.0121 (4)0.0111 (4)0.0126 (4)0.0006 (3)0.0043 (3)0.0047 (3)
Geometric parameters (Å, º) top
S1—C81.7099 (10)C1—H1A0.9300
O1—C61.3701 (11)C2—C31.3912 (13)
O1—C71.4370 (12)C2—H2A0.9300
N1—C81.3384 (12)C3—C41.3988 (13)
N1—C31.4284 (12)C4—C51.3868 (13)
N1—H1B0.881 (17)C4—H4A0.9300
N2—C81.3331 (12)C5—C61.3997 (13)
N2—H2B0.861 (17)C5—H5A0.9300
N2—H2C0.886 (16)C7—H7A0.9600
C1—C21.3932 (13)C7—H7B0.9600
C1—C61.3961 (13)C7—H7C0.9600
C6—O1—C7115.68 (8)C5—C4—H4A119.9
C8—N1—C3125.90 (8)C3—C4—H4A119.9
C8—N1—H1B117.5 (11)C4—C5—C6119.95 (9)
C3—N1—H1B116.2 (11)C4—C5—H5A120.0
C8—N2—H2B123.1 (11)C6—C5—H5A120.0
C8—N2—H2C117.6 (10)O1—C6—C1123.84 (9)
H2B—N2—H2C119.3 (15)O1—C6—C5116.04 (8)
C2—C1—C6119.52 (9)C1—C6—C5120.12 (9)
C2—C1—H1A120.2O1—C7—H7A109.5
C6—C1—H1A120.2O1—C7—H7B109.5
C3—C2—C1120.51 (9)H7A—C7—H7B109.5
C3—C2—H2A119.7O1—C7—H7C109.5
C1—C2—H2A119.7H7A—C7—H7C109.5
C2—C3—C4119.75 (9)H7B—C7—H7C109.5
C2—C3—N1119.03 (8)N2—C8—N1119.50 (9)
C4—C3—N1121.15 (8)N2—C8—S1120.73 (7)
C5—C4—C3120.11 (9)N1—C8—S1119.77 (7)
C6—C1—C2—C31.07 (15)C7—O1—C6—C14.83 (14)
C1—C2—C3—C40.53 (15)C7—O1—C6—C5175.51 (8)
C1—C2—C3—N1177.60 (9)C2—C1—C6—O1178.78 (9)
C8—N1—C3—C2121.27 (11)C2—C1—C6—C51.57 (14)
C8—N1—C3—C461.70 (14)C4—C5—C6—O1179.86 (8)
C2—C3—C4—C51.65 (14)C4—C5—C6—C10.46 (15)
N1—C3—C4—C5178.65 (9)C3—N1—C8—N21.12 (15)
C3—C4—C5—C61.15 (15)C3—N1—C8—S1179.06 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1i0.88 (2)2.420 (19)3.2787 (10)166 (2)
N2—H2B···O1ii0.86 (2)2.348 (19)3.0512 (12)139 (2)
N2—H2C···S1iii0.88 (2)2.511 (18)3.3870 (10)172 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z; (iii) x+2, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds