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The title compound, C10H8N4O3S, is almost planar [dihedral angle between the rings = 2.2 (2)°; r.m.s. deviation for the non-H atoms = 0.050 Å]. In the crystal, C—H...O and C—H...N hydrogen bonds link the mol­ecules into (10-2) layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431461701121X/hb4161sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431461701121X/hb4161Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S241431461701121X/hb4161Isup3.cml
Supplementary material

CCDC reference: 1565676

Key indicators

  • Single-crystal X-ray study
  • T = 85 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.092
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

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Alert level B PLAT915_ALERT_3_B No Flack x Check Done: Low Friedel Pair Coverage 45 %
Author Response: Due to the absence of anomalous scatterers, the absolute structure cannot be inequivocally determined. Flack parameter is quite close to 0 (the esd is high): Flack x = 0.080(143) by hole-in-one fit to all intensities

Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low . 0.977 Note PLAT034_ALERT_1_C No Flack Parameter Given. Z > Si, NonCentro .... Please Do ! PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.50 Note PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.006 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.66 Ang. PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 20 Report
Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 9 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 9 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 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 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction Ltd, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction Ltd, 2008); data reduction: CrysAlis CCD (Oxford Diffraction Ltd, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

N-Methyl-4-(4-nitrophenyl)-N-nitroso-1,3-thiazol-2-amine top
Crystal data top
C10H8N4O3SF(000) = 272
Mr = 264.26Dx = 1.578 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 4.7729 (3) ÅCell parameters from 2950 reflections
b = 13.7362 (8) Åθ = 3.8–25.9°
c = 8.5391 (4) ŵ = 0.30 mm1
β = 96.576 (5)°T = 85 K
V = 556.15 (5) Å3Irregular, yellow
Z = 20.28 × 0.17 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1θmax = 25.9°, θmin = 3.8°
ω scanh = 55
2950 measured reflectionsk = 1516
1557 independent reflectionsl = 1010
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.061P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1557 reflectionsΔρmax = 0.29 e Å3
164 parametersΔρmin = 0.36 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were found in a difference map but set to idealized positions and treated as riding with CAr—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) and with C—H3 = 0.96 Å and Uiso(H) = 1.5Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.4840 (8)0.8638 (2)0.9230 (4)0.0325 (8)
O20.3222 (7)0.4737 (2)0.2371 (4)0.0354 (9)
O30.4836 (8)0.5884 (2)0.0786 (4)0.0351 (8)
N10.7254 (8)0.7692 (3)0.5950 (4)0.0224 (8)
N21.1208 (8)0.8118 (2)0.7699 (4)0.0232 (8)
N31.2871 (9)0.8869 (3)0.8228 (5)0.0292 (9)
N40.3161 (8)0.5566 (3)0.1862 (4)0.0264 (9)
S10.8523 (3)0.95119 (7)0.57753 (16)0.0281 (3)
C10.9010 (9)0.8347 (3)0.6527 (5)0.0234 (9)
C20.5680 (10)0.9071 (3)0.4564 (6)0.0259 (10)
H20.45320.94460.38450.031*
C30.5332 (9)0.8101 (3)0.4796 (5)0.0232 (10)
C41.1769 (10)0.7131 (3)0.8266 (6)0.0283 (11)
H4A1.02920.67070.78160.042*
H4B1.18440.71190.93940.042*
H4C1.35410.69140.79620.042*
C50.3134 (9)0.7463 (3)0.3993 (5)0.0226 (9)
C60.1112 (10)0.7803 (3)0.2801 (5)0.0245 (10)
H60.11610.84490.24790.029*
C70.0955 (10)0.7190 (3)0.2098 (5)0.0239 (10)
H70.23080.74170.13130.029*
C80.0967 (9)0.6235 (3)0.2586 (5)0.0239 (9)
C90.1000 (10)0.5865 (3)0.3759 (5)0.0251 (10)
H90.09330.52180.40710.030*
C100.3061 (10)0.6486 (3)0.4452 (5)0.0240 (10)
H100.44140.62520.52310.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.028 (2)0.0342 (18)0.0326 (18)0.0001 (15)0.0093 (15)0.0021 (13)
O20.035 (2)0.0262 (18)0.041 (2)0.0025 (15)0.0119 (17)0.0011 (14)
O30.031 (2)0.0381 (18)0.0320 (18)0.0002 (15)0.0151 (15)0.0006 (14)
N10.0174 (19)0.0251 (17)0.0237 (19)0.0004 (15)0.0017 (15)0.0020 (14)
N20.022 (2)0.0225 (18)0.0244 (19)0.0031 (15)0.0008 (16)0.0009 (15)
N30.028 (2)0.029 (2)0.0294 (19)0.0030 (18)0.0044 (18)0.0019 (16)
N40.021 (2)0.030 (2)0.028 (2)0.0011 (17)0.0035 (16)0.0048 (16)
S10.0237 (6)0.0235 (5)0.0356 (6)0.0012 (5)0.0033 (4)0.0000 (5)
C10.015 (2)0.024 (2)0.031 (2)0.0013 (18)0.0042 (18)0.0007 (18)
C20.017 (3)0.031 (2)0.029 (2)0.0019 (19)0.0001 (19)0.0019 (19)
C30.019 (3)0.024 (2)0.027 (2)0.0019 (18)0.0043 (19)0.0015 (18)
C40.027 (3)0.026 (2)0.031 (2)0.0021 (19)0.004 (2)0.0017 (19)
C50.016 (2)0.030 (2)0.021 (2)0.0036 (18)0.0023 (18)0.0014 (16)
C60.024 (2)0.023 (2)0.027 (2)0.0039 (18)0.0051 (19)0.0049 (18)
C70.021 (2)0.027 (2)0.023 (2)0.0029 (19)0.0018 (18)0.0015 (17)
C80.017 (2)0.030 (2)0.024 (2)0.0011 (18)0.0027 (18)0.0032 (18)
C90.028 (3)0.022 (2)0.025 (2)0.002 (2)0.0001 (19)0.0019 (17)
C100.019 (3)0.025 (2)0.026 (2)0.0030 (18)0.0040 (18)0.0016 (17)
Geometric parameters (Å, º) top
O1—N31.238 (5)C4—H4A0.9600
O2—N41.220 (4)C4—H4B0.9600
O3—N41.227 (5)C4—H4C0.9600
N1—C11.288 (6)C5—C101.399 (6)
N1—C31.386 (6)C5—C61.400 (6)
N2—N31.348 (5)C6—C71.381 (6)
N2—C11.401 (5)C6—H60.9300
N2—C41.454 (5)C7—C81.376 (6)
N4—C81.475 (5)C7—H70.9300
S1—C21.720 (5)C8—C91.388 (6)
S1—C11.730 (4)C9—C101.383 (6)
C2—C31.359 (6)C9—H90.9300
C2—H20.9300C10—H100.9300
C3—C51.475 (6)
C1—N1—C3109.7 (3)N2—C4—H4C109.5
N3—N2—C1115.6 (3)H4A—C4—H4C109.5
N3—N2—C4121.6 (4)H4B—C4—H4C109.5
C1—N2—C4122.8 (3)C10—C5—C6119.1 (4)
O1—N3—N2114.0 (3)C10—C5—C3118.6 (4)
O2—N4—O3124.0 (4)C6—C5—C3122.3 (4)
O2—N4—C8118.5 (4)C7—C6—C5120.7 (4)
O3—N4—C8117.5 (4)C7—C6—H6119.6
C2—S1—C187.7 (2)C5—C6—H6119.6
N1—C1—N2121.2 (4)C8—C7—C6118.5 (4)
N1—C1—S1116.8 (4)C8—C7—H7120.7
N2—C1—S1122.0 (3)C6—C7—H7120.7
C3—C2—S1111.0 (4)C7—C8—C9122.7 (4)
C3—C2—H2124.5C7—C8—N4119.6 (4)
S1—C2—H2124.5C9—C8—N4117.6 (4)
C2—C3—N1114.8 (4)C10—C9—C8118.2 (4)
C2—C3—C5127.4 (4)C10—C9—H9120.9
N1—C3—C5117.8 (3)C8—C9—H9120.9
N2—C4—H4A109.5C9—C10—C5120.7 (4)
N2—C4—H4B109.5C9—C10—H10119.6
H4A—C4—H4B109.5C5—C10—H10119.6
C1—N2—N3—O1178.1 (4)C2—C3—C5—C62.2 (6)
C4—N2—N3—O10.9 (6)N1—C3—C5—C6179.4 (4)
C3—N1—C1—N2178.9 (3)C10—C5—C6—C70.9 (6)
C3—N1—C1—S10.8 (5)C3—C5—C6—C7178.5 (4)
N3—N2—C1—N1178.8 (4)C5—C6—C7—C80.5 (6)
C4—N2—C1—N14.1 (6)C6—C7—C8—C90.4 (6)
N3—N2—C1—S11.6 (5)C6—C7—C8—N4179.6 (4)
C4—N2—C1—S1175.6 (4)O2—N4—C8—C7176.1 (4)
C2—S1—C1—N10.1 (4)O3—N4—C8—C73.3 (6)
C2—S1—C1—N2179.5 (4)O2—N4—C8—C93.2 (6)
C1—S1—C2—C30.6 (4)O3—N4—C8—C9177.4 (4)
S1—C2—C3—N11.2 (5)C7—C8—C9—C100.5 (6)
S1—C2—C3—C5179.7 (3)N4—C8—C9—C10179.8 (4)
C1—N1—C3—C21.3 (5)C8—C9—C10—C50.8 (6)
C1—N1—C3—C5179.9 (4)C6—C5—C10—C91.0 (6)
C2—C3—C5—C10177.2 (4)C3—C5—C10—C9178.4 (4)
N1—C3—C5—C101.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.663.182 (6)117
C2—H2···N3i0.932.483.280 (6)144
C4—H4A···O2ii0.962.603.525 (5)163
C4—H4B···O3iii0.962.523.065 (6)116
Symmetry codes: (i) x1, y+2, z1/2; (ii) x+1, y+1, z+1/2; (iii) x+2, y, z+1.
 

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