Download citation
Download citation
link to html
The mol­ecule of the title compound, C10H10N2OS, is not planar, with a dihedral angle of 14.8 (2)° between the planes of the benzene and thia­zole rings. Mol­ecules are linked by inter­molecular N—H...O and N—H...N hydrogen bonds between the amino H atoms and O and N atoms of the meth­oxy group and thia­zole ring, respectively, forming an infinite chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010610/at2018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010610/at2018Isup2.hkl
Contains datablock I

CCDC reference: 604958

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.068
  • wR factor = 0.187
  • Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05 PLAT128_ALERT_4_C Non-standard setting of Space group Pna21 .... Pn21a PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 70.76 From the CIF: _reflns_number_total 1034 Count of symmetry unique reflns 1034 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Amino-4-(4'-methoxyphenyl)-1,3-thiazole top
Crystal data top
C10H10N2OSF(000) = 432
Mr = 206.26Dx = 1.368 Mg m3
Orthorhombic, Pn21aCu Kα radiation, λ = 1.54184 Å
Hall symbol: P -2ac -2nCell parameters from 25 reflections
a = 7.181 (2) Åθ = 2.6–28.3°
b = 7.750 (2) ŵ = 2.61 mm1
c = 17.994 (3) ÅT = 296 K
V = 1001.4 (4) Å3Plate, colorless
Z = 40.35 × 0.25 × 0.10 mm
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer
847 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 70.8°, θmin = 4.9°
Non–profiled ω scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 09
Tmin = 0.475, Tmax = 0.768l = 220
1034 measured reflections3 standard reflections every 120 min
1034 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.187 w = 1/[σ2(Fo2) + (0.1346P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1034 reflectionsΔρmax = 0.65 e Å3
127 parametersΔρmin = 0.32 e Å3
1 restraintAbsolute structure: Flack (1983), with 0 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
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
S10.2699 (2)0.4471 (3)0.32537 (10)0.0601 (6)
O1.0390 (6)0.5359 (8)0.6520 (2)0.0608 (13)
N0.3998 (7)0.7076 (8)0.2413 (3)0.0521 (14)
N30.5647 (6)0.6284 (7)0.3491 (2)0.0398 (11)
H10.47750.78840.23070.063*
H20.30560.68900.21280.063*
C20.4257 (7)0.6096 (8)0.3027 (3)0.0391 (12)
C40.5454 (8)0.5150 (8)0.4088 (3)0.0395 (12)
C50.4009 (9)0.4070 (9)0.4040 (4)0.0558 (18)
H50.37430.32130.43860.067*
C60.6811 (8)0.5214 (9)0.4704 (3)0.0390 (12)
C70.6429 (8)0.4393 (11)0.5375 (3)0.0501 (14)
H70.53320.37650.54250.060*
C80.7639 (9)0.4491 (13)0.5969 (3)0.0520 (15)
H80.73290.39680.64180.062*
C90.9322 (9)0.5368 (10)0.5901 (3)0.0493 (15)
C100.9713 (8)0.6198 (10)0.5243 (3)0.0483 (14)
H101.08140.68200.51940.058*
C110.8471 (8)0.6111 (10)0.4651 (3)0.0447 (13)
H110.87640.66700.42090.054*
C121.2075 (11)0.6320 (16)0.6515 (4)0.076 (3)
H12A1.26960.61850.69840.114*
H12B1.18020.75170.64340.114*
H12C1.28670.59060.61240.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0532 (9)0.0602 (9)0.0669 (10)0.0194 (10)0.0176 (7)0.0104 (10)
O0.060 (3)0.069 (3)0.053 (2)0.010 (3)0.017 (2)0.015 (3)
N0.048 (3)0.069 (4)0.039 (3)0.011 (3)0.011 (2)0.009 (3)
N30.036 (2)0.049 (3)0.035 (2)0.000 (2)0.0029 (17)0.001 (2)
C20.041 (3)0.044 (3)0.032 (2)0.002 (3)0.004 (2)0.008 (2)
C40.039 (3)0.038 (3)0.042 (3)0.003 (2)0.006 (2)0.002 (2)
C50.052 (4)0.050 (4)0.065 (4)0.016 (3)0.013 (3)0.011 (3)
C60.041 (3)0.040 (3)0.036 (3)0.003 (2)0.005 (2)0.000 (2)
C70.050 (3)0.046 (3)0.054 (3)0.002 (4)0.008 (2)0.006 (3)
C80.062 (3)0.052 (3)0.041 (3)0.014 (4)0.003 (2)0.016 (4)
C90.055 (4)0.047 (3)0.046 (3)0.010 (3)0.002 (3)0.000 (3)
C100.041 (3)0.055 (4)0.049 (3)0.008 (3)0.004 (2)0.004 (3)
C110.047 (3)0.053 (3)0.034 (3)0.005 (3)0.001 (2)0.004 (3)
C120.068 (5)0.096 (7)0.064 (4)0.019 (5)0.019 (4)0.001 (5)
Geometric parameters (Å, º) top
S1—C51.728 (7)C7—C81.379 (8)
S1—C21.733 (6)C7—C61.393 (8)
O—C91.353 (7)C7—H70.9300
O—C121.421 (10)C8—H80.9300
N—C21.353 (8)C9—C101.376 (8)
N—H10.8600C9—C81.392 (10)
N—H20.8600C10—C111.390 (8)
N3—C21.310 (7)C10—H100.9300
N3—C41.395 (7)C11—H110.9300
C4—C51.336 (8)C12—H12A0.9600
C5—H50.9300C12—H12B0.9600
C6—C111.383 (9)C12—H12C0.9600
C6—C41.477 (8)
C5—S1—C288.4 (3)C6—C7—H7119.2
C9—O—C12118.4 (6)C7—C8—C9120.3 (6)
C2—N—H1120.0C7—C8—H8119.8
C2—N—H2120.0C9—C8—H8119.8
H1—N—H2120.0O—C9—C10126.5 (6)
C2—N3—C4110.2 (5)O—C9—C8114.6 (6)
N3—C2—N124.3 (6)C10—C9—C8118.8 (6)
N3—C2—S1115.0 (4)C9—C10—C11120.3 (6)
N—C2—S1120.7 (4)C9—C10—H10119.8
C5—C4—N3114.9 (5)C11—C10—H10119.8
C5—C4—C6125.6 (6)C6—C11—C10121.6 (5)
N3—C4—C6119.4 (5)C6—C11—H11119.2
C4—C5—S1111.3 (5)C10—C11—H11119.2
C4—C5—H5124.3O—C12—H12A109.5
S1—C5—H5124.3O—C12—H12B109.5
C11—C6—C7117.3 (5)H12A—C12—H12B109.5
C11—C6—C4122.3 (5)O—C12—H12C109.5
C7—C6—C4120.4 (5)H12A—C12—H12C109.5
C8—C7—C6121.5 (6)H12B—C12—H12C109.5
C8—C7—H7119.2
C2—S1—C5—C41.0 (5)C7—C6—C11—C100.1 (10)
C5—S1—C2—N31.3 (5)C7—C6—C4—N3165.3 (6)
C5—S1—C2—N178.2 (6)C11—C6—C4—C5166.7 (6)
C12—O—C9—C101.5 (12)C11—C6—C4—N313.0 (9)
C12—O—C9—C8175.9 (8)C8—C7—C6—C111.0 (10)
C2—N3—C4—C53.9 (7)C8—C7—C6—C4177.4 (8)
C2—N3—C4—C6176.3 (5)O—C9—C10—C11179.3 (7)
C4—N3—C2—N176.4 (6)C6—C7—C8—C92.4 (12)
C4—N3—C2—S13.1 (6)O—C9—C8—C7179.5 (8)
N3—C4—C5—S13.0 (7)C8—C9—C10—C112.0 (11)
C6—C4—C5—S1177.3 (5)C10—C9—C8—C72.9 (12)
C4—C6—C11—C10178.3 (7)C9—C10—C11—C60.6 (11)
C7—C6—C4—C515.0 (9)
 

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