Download citation
Download citation
link to html
In the title compound, C8H10N2OS, the dihedral angle between the benzene ring and the thio­urea group is 65.33 (2)°. Mol­ecules are linked into infinite chains along the a axis by inter­molecular N—H...O/S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049002/ci2223sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049002/ci2223Isup2.hkl
Contains datablock I

CCDC reference: 629629

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.026
  • wR factor = 0.079
  • Data-to-parameter ratio = 36.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N2 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 3 Indicator that the structure quality may be low 2 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 M. M. Rosli 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-(2-Methoxyphenyl)thiourea top
Crystal data top
C8H10N2OSF(000) = 384
Mr = 182.24Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8578 reflections
a = 7.3389 (1) Åθ = 2.8–37.5°
b = 13.6979 (2) ŵ = 0.33 mm1
c = 10.5491 (1) ÅT = 100 K
β = 126.747 (1)°Block, colourless
V = 849.74 (2) Å30.61 × 0.35 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4439 independent reflections
Radiation source: fine-focus sealed tube4202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 37.5°, θmin = 2.8°
ω scansh = 1112
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2323
Tmin = 0.823, Tmax = 0.937l = 1817
35595 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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.1918P]
where P = (Fo2 + 2Fc2)/3
4439 reflections(Δ/σ)max = 0.001
122 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
S10.06331 (2)0.566374 (10)0.342328 (16)0.01212 (4)
O10.61672 (7)0.39615 (3)0.82218 (5)0.01331 (7)
N10.23857 (8)0.40603 (4)0.51695 (6)0.01151 (8)
N20.32350 (9)0.43304 (4)0.34138 (6)0.01323 (8)
C10.55719 (9)0.31234 (4)0.73595 (6)0.01110 (8)
C20.67495 (10)0.22425 (4)0.79599 (7)0.01368 (9)
H2A0.80030.21990.90160.016*
C30.60489 (10)0.14280 (4)0.69775 (7)0.01491 (9)
H3A0.68430.08440.73850.018*
C40.41765 (10)0.14798 (4)0.53962 (7)0.01489 (9)
H4A0.37370.09380.47410.018*
C50.29645 (9)0.23530 (4)0.48034 (7)0.01324 (9)
H5A0.16900.23880.37530.016*
C60.36449 (9)0.31721 (4)0.57686 (6)0.01080 (8)
C70.21866 (8)0.46173 (4)0.40453 (6)0.01018 (8)
C80.82632 (10)0.39312 (5)0.97973 (7)0.01656 (10)
H8A0.85200.45521.03000.025*
H8B0.94980.37880.97460.025*
H8C0.81700.34331.03970.025*
H1N10.166 (2)0.4243 (9)0.5522 (16)0.026 (3)*
H1N20.335 (2)0.4762 (9)0.2839 (14)0.022 (3)*
H2N20.424 (2)0.3861 (10)0.3887 (15)0.029 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01270 (6)0.01114 (6)0.01205 (6)0.00262 (4)0.00716 (5)0.00229 (4)
O10.01354 (16)0.01261 (17)0.01103 (15)0.00046 (12)0.00588 (13)0.00081 (12)
N10.01198 (17)0.01178 (18)0.01166 (17)0.00306 (13)0.00754 (14)0.00276 (13)
N20.01397 (19)0.0141 (2)0.01407 (18)0.00235 (14)0.00970 (16)0.00185 (14)
C10.01082 (18)0.01130 (19)0.01084 (18)0.00059 (14)0.00631 (15)0.00115 (14)
C20.01265 (19)0.0127 (2)0.0135 (2)0.00228 (15)0.00666 (17)0.00314 (16)
C30.0147 (2)0.0112 (2)0.0183 (2)0.00220 (16)0.00956 (18)0.00255 (17)
C40.0149 (2)0.0110 (2)0.0178 (2)0.00040 (16)0.00929 (19)0.00105 (17)
C50.01184 (19)0.0123 (2)0.0133 (2)0.00037 (15)0.00626 (16)0.00069 (16)
C60.01002 (17)0.01052 (19)0.01118 (18)0.00123 (14)0.00598 (15)0.00153 (14)
C70.00873 (17)0.01089 (19)0.00905 (17)0.00006 (14)0.00431 (14)0.00001 (14)
C80.0137 (2)0.0205 (3)0.0119 (2)0.00035 (18)0.00581 (17)0.00217 (17)
Geometric parameters (Å, º) top
S1—C71.7000 (5)C2—C31.3948 (9)
O1—C11.3641 (7)C2—H2A0.93
O1—C81.4391 (7)C3—C41.3904 (9)
N1—C71.3426 (7)C3—H3A0.93
N1—C61.4264 (7)C4—C51.3954 (8)
N1—H1N10.848 (14)C4—H4A0.93
N2—C71.3429 (7)C5—C61.3917 (8)
N2—H1N20.886 (12)C5—H5A0.93
N2—H2N20.874 (14)C8—H8A0.96
C1—C21.3961 (8)C8—H8B0.96
C1—C61.4075 (7)C8—H8C0.96
C1—O1—C8116.13 (5)C3—C4—H4A120.4
C7—N1—C6125.13 (5)C5—C4—H4A120.4
C7—N1—H1N1117.0 (9)C6—C5—C4120.65 (5)
C6—N1—H1N1117.8 (9)C6—C5—H5A119.7
C7—N2—H1N2117.5 (8)C4—C5—H5A119.7
C7—N2—H2N2117.9 (9)C5—C6—C1119.93 (5)
H1N2—N2—H2N2119.2 (12)C5—C6—N1120.65 (5)
O1—C1—C2124.09 (5)C1—C6—N1119.42 (5)
O1—C1—C6116.59 (5)N1—C7—N2118.69 (5)
C2—C1—C6119.31 (5)N1—C7—S1120.90 (4)
C3—C2—C1120.09 (5)N2—C7—S1120.41 (4)
C3—C2—H2A120.0O1—C8—H8A109.5
C1—C2—H2A120.0O1—C8—H8B109.5
C4—C3—C2120.73 (5)H8A—C8—H8B109.5
C4—C3—H3A119.6O1—C8—H8C109.5
C2—C3—H3A119.6H8A—C8—H8C109.5
C3—C4—C5119.26 (5)H8B—C8—H8C109.5
C8—O1—C1—C25.88 (8)O1—C1—C6—C5178.45 (5)
C8—O1—C1—C6174.04 (5)C2—C1—C6—C51.47 (8)
O1—C1—C2—C3178.36 (5)O1—C1—C6—N12.56 (7)
C6—C1—C2—C31.56 (8)C2—C1—C6—N1177.51 (5)
C1—C2—C3—C40.13 (9)C7—N1—C6—C566.27 (8)
C2—C3—C4—C51.40 (9)C7—N1—C6—C1114.75 (6)
C3—C4—C5—C61.49 (9)C6—N1—C7—N20.16 (8)
C4—C5—C6—C10.05 (8)C6—N1—C7—S1179.95 (4)
C4—C5—C6—N1179.02 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···S1i0.85 (2)2.515 (17)3.3452 (7)166 (1)
N2—H1N2···O1ii0.89 (1)2.216 (13)3.0903 (8)169 (1)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, 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