N-(4-Methoxy­phen­yl)thio­urea

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.

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

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

Crystal data

C8H10N2OS	Z = 2
Mr = 182.24	F(000) = 192
Triclinic, P1	Dx = 1.385 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7328 (2) Å	Cell parameters from 6119 reflections
b = 8.3813 (2) Å	θ = 2.6–30.0°
c = 9.0571 (2) Å	µ = 0.32 mm^−1
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) Å^3

Data collection

Brucker SMART APEX2 CCD diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	2432 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.6°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.853, Tmax = 0.913	l = −12→12
4876 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 0.1605P] where P = (Fo^2 + 2Fc^2)/3
2531 reflections	(Δ/σ)max < 0.001
122 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.03388 (4)	0.22141 (3)	0.54932 (3)	0.01413 (8)
O1	0.39369 (11)	0.84909 (10)	−0.12690 (9)	0.01608 (15)
N1	0.83759 (14)	0.48002 (11)	0.35198 (11)	0.01420 (16)
N2	0.85042 (14)	0.21414 (11)	0.33120 (11)	0.01551 (17)
C1	0.70653 (15)	0.82462 (13)	−0.03598 (12)	0.01485 (18)
H1A	0.7651	0.9289	−0.1304	0.018*
C2	0.81435 (15)	0.72727 (13)	0.08457 (13)	0.01501 (18)
H2A	0.9463	0.7658	0.0693	0.018*
C3	0.72618 (15)	0.57281 (12)	0.22756 (12)	0.01257 (17)
C4	0.52703 (15)	0.51556 (13)	0.25123 (12)	0.01478 (18)
H4A	0.4662	0.4140	0.3482	0.018*
C5	0.42008 (15)	0.60994 (13)	0.13037 (13)	0.01515 (18)
H5A	0.2887	0.5706	0.1452	0.018*
C6	0.50999 (15)	0.76453 (12)	−0.01401 (12)	0.01300 (17)
C7	0.49334 (17)	0.99992 (14)	−0.28097 (13)	0.01800 (19)
H7A	0.4009	1.0487	−0.3522	0.027*
H7B	0.6188	0.9632	−0.3419	0.027*
H7C	0.5268	1.0886	−0.2518	0.027*
C8	0.89783 (14)	0.31099 (12)	0.40008 (12)	0.01178 (17)
H1B	0.882 (3)	0.544 (2)	0.391 (2)	0.029 (4)*
H2B	0.786 (3)	0.256 (2)	0.253 (2)	0.026 (4)*
H2C	0.892 (3)	0.103 (2)	0.365 (2)	0.023 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01846 (13)	0.00991 (12)	0.01816 (13)	0.00165 (8)	−0.01189 (9)	−0.00562 (9)
O1	0.0164 (3)	0.0158 (3)	0.0157 (3)	−0.0002 (2)	−0.0099 (3)	−0.0029 (3)
N1	0.0199 (4)	0.0106 (3)	0.0169 (4)	0.0027 (3)	−0.0120 (3)	−0.0063 (3)
N2	0.0222 (4)	0.0121 (4)	0.0184 (4)	0.0038 (3)	−0.0129 (3)	−0.0082 (3)
C1	0.0150 (4)	0.0139 (4)	0.0145 (4)	−0.0008 (3)	−0.0064 (3)	−0.0034 (3)
C2	0.0142 (4)	0.0142 (4)	0.0173 (4)	−0.0002 (3)	−0.0078 (3)	−0.0051 (3)
C3	0.0153 (4)	0.0113 (4)	0.0141 (4)	0.0027 (3)	−0.0077 (3)	−0.0063 (3)
C4	0.0157 (4)	0.0126 (4)	0.0150 (4)	0.0000 (3)	−0.0058 (3)	−0.0040 (3)
C5	0.0135 (4)	0.0148 (4)	0.0172 (4)	−0.0004 (3)	−0.0067 (3)	−0.0052 (3)
C6	0.0140 (4)	0.0138 (4)	0.0135 (4)	0.0024 (3)	−0.0073 (3)	−0.0063 (3)
C7	0.0211 (5)	0.0169 (4)	0.0150 (4)	−0.0003 (4)	−0.0095 (4)	−0.0031 (4)
C8	0.0121 (4)	0.0111 (4)	0.0126 (4)	−0.0006 (3)	−0.0043 (3)	−0.0047 (3)

Geometric parameters (Å, º)

S1—C8	1.7099 (10)	C1—H1A	0.9300
O1—C6	1.3701 (11)	C2—C3	1.3912 (13)
O1—C7	1.4370 (12)	C2—H2A	0.9300
N1—C8	1.3384 (12)	C3—C4	1.3988 (13)
N1—C3	1.4284 (12)	C4—C5	1.3868 (13)
N1—H1B	0.881 (17)	C4—H4A	0.9300
N2—C8	1.3331 (12)	C5—C6	1.3997 (13)
N2—H2B	0.861 (17)	C5—H5A	0.9300
N2—H2C	0.886 (16)	C7—H7A	0.9600
C1—C2	1.3932 (13)	C7—H7B	0.9600
C1—C6	1.3961 (13)	C7—H7C	0.9600
C6—O1—C7	115.68 (8)	C5—C4—H4A	119.9
C8—N1—C3	125.90 (8)	C3—C4—H4A	119.9
C8—N1—H1B	117.5 (11)	C4—C5—C6	119.95 (9)
C3—N1—H1B	116.2 (11)	C4—C5—H5A	120.0
C8—N2—H2B	123.1 (11)	C6—C5—H5A	120.0
C8—N2—H2C	117.6 (10)	O1—C6—C1	123.84 (9)
H2B—N2—H2C	119.3 (15)	O1—C6—C5	116.04 (8)
C2—C1—C6	119.52 (9)	C1—C6—C5	120.12 (9)
C2—C1—H1A	120.2	O1—C7—H7A	109.5
C6—C1—H1A	120.2	O1—C7—H7B	109.5
C3—C2—C1	120.51 (9)	H7A—C7—H7B	109.5
C3—C2—H2A	119.7	O1—C7—H7C	109.5
C1—C2—H2A	119.7	H7A—C7—H7C	109.5
C2—C3—C4	119.75 (9)	H7B—C7—H7C	109.5
C2—C3—N1	119.03 (8)	N2—C8—N1	119.50 (9)
C4—C3—N1	121.15 (8)	N2—C8—S1	120.73 (7)
C5—C4—C3	120.11 (9)	N1—C8—S1	119.77 (7)
C6—C1—C2—C3	−1.07 (15)	C7—O1—C6—C1	4.83 (14)
C1—C2—C3—C4	−0.53 (15)	C7—O1—C6—C5	−175.51 (8)
C1—C2—C3—N1	−177.60 (9)	C2—C1—C6—O1	−178.78 (9)
C8—N1—C3—C2	−121.27 (11)	C2—C1—C6—C5	1.57 (14)
C8—N1—C3—C4	61.70 (14)	C4—C5—C6—O1	179.86 (8)
C2—C3—C4—C5	1.65 (14)	C4—C5—C6—C1	−0.46 (15)
N1—C3—C4—C5	178.65 (9)	C3—N1—C8—N2	−1.12 (15)
C3—C4—C5—C6	−1.15 (15)	C3—N1—C8—S1	179.06 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1^i	0.88 (2)	2.420 (19)	3.2787 (10)	166 (2)
N2—H2B···O1^ii	0.86 (2)	2.348 (19)	3.0512 (12)	139 (2)
N2—H2C···S1^iii	0.88 (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.