The title compound, C
10H
8N
4O
3S, 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
CCDC reference: 1565676
Key indicators
- Single-crystal X-ray study
- T = 85 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.092
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
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
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
C10H8N4O3S | F(000) = 272 |
Mr = 264.26 | Dx = 1.578 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7729 (3) Å | Cell parameters from 2950 reflections |
b = 13.7362 (8) Å | θ = 3.8–25.9° |
c = 8.5391 (4) Å | µ = 0.30 mm−1 |
β = 96.576 (5)° | T = 85 K |
V = 556.15 (5) Å3 | Irregular, yellow |
Z = 2 | 0.28 × 0.17 × 0.15 mm |
Data collection top
Oxford Diffraction Xcalibur diffractometer | 1320 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1 | θmax = 25.9°, θmin = 3.8° |
ω scan | h = −5→5 |
2950 measured reflections | k = −15→16 |
1557 independent reflections | l = −10→10 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.29 e Å−3 |
164 parameters | Δρmin = −0.36 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.4840 (8) | 0.8638 (2) | 0.9230 (4) | 0.0325 (8) | |
O2 | −0.3222 (7) | 0.4737 (2) | 0.2371 (4) | 0.0354 (9) | |
O3 | −0.4836 (8) | 0.5884 (2) | 0.0786 (4) | 0.0351 (8) | |
N1 | 0.7254 (8) | 0.7692 (3) | 0.5950 (4) | 0.0224 (8) | |
N2 | 1.1208 (8) | 0.8118 (2) | 0.7699 (4) | 0.0232 (8) | |
N3 | 1.2871 (9) | 0.8869 (3) | 0.8228 (5) | 0.0292 (9) | |
N4 | −0.3161 (8) | 0.5566 (3) | 0.1862 (4) | 0.0264 (9) | |
S1 | 0.8523 (3) | 0.95119 (7) | 0.57753 (16) | 0.0281 (3) | |
C1 | 0.9010 (9) | 0.8347 (3) | 0.6527 (5) | 0.0234 (9) | |
C2 | 0.5680 (10) | 0.9071 (3) | 0.4564 (6) | 0.0259 (10) | |
H2 | 0.4532 | 0.9446 | 0.3845 | 0.031* | |
C3 | 0.5332 (9) | 0.8101 (3) | 0.4796 (5) | 0.0232 (10) | |
C4 | 1.1769 (10) | 0.7131 (3) | 0.8266 (6) | 0.0283 (11) | |
H4A | 1.0292 | 0.6707 | 0.7816 | 0.042* | |
H4B | 1.1844 | 0.7119 | 0.9394 | 0.042* | |
H4C | 1.3541 | 0.6914 | 0.7962 | 0.042* | |
C5 | 0.3134 (9) | 0.7463 (3) | 0.3993 (5) | 0.0226 (9) | |
C6 | 0.1112 (10) | 0.7803 (3) | 0.2801 (5) | 0.0245 (10) | |
H6 | 0.1161 | 0.8449 | 0.2479 | 0.029* | |
C7 | −0.0955 (10) | 0.7190 (3) | 0.2098 (5) | 0.0239 (10) | |
H7 | −0.2308 | 0.7417 | 0.1313 | 0.029* | |
C8 | −0.0967 (9) | 0.6235 (3) | 0.2586 (5) | 0.0239 (9) | |
C9 | 0.1000 (10) | 0.5865 (3) | 0.3759 (5) | 0.0251 (10) | |
H9 | 0.0933 | 0.5218 | 0.4071 | 0.030* | |
C10 | 0.3061 (10) | 0.6486 (3) | 0.4452 (5) | 0.0240 (10) | |
H10 | 0.4414 | 0.6252 | 0.5231 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.028 (2) | 0.0342 (18) | 0.0326 (18) | 0.0001 (15) | −0.0093 (15) | −0.0021 (13) |
O2 | 0.035 (2) | 0.0262 (18) | 0.041 (2) | −0.0025 (15) | −0.0119 (17) | −0.0011 (14) |
O3 | 0.031 (2) | 0.0381 (18) | 0.0320 (18) | −0.0002 (15) | −0.0151 (15) | −0.0006 (14) |
N1 | 0.0174 (19) | 0.0251 (17) | 0.0237 (19) | 0.0004 (15) | −0.0017 (15) | −0.0020 (14) |
N2 | 0.022 (2) | 0.0225 (18) | 0.0244 (19) | −0.0031 (15) | −0.0008 (16) | −0.0009 (15) |
N3 | 0.028 (2) | 0.029 (2) | 0.0294 (19) | −0.0030 (18) | −0.0044 (18) | −0.0019 (16) |
N4 | 0.021 (2) | 0.030 (2) | 0.028 (2) | 0.0011 (17) | −0.0035 (16) | −0.0048 (16) |
S1 | 0.0237 (6) | 0.0235 (5) | 0.0356 (6) | −0.0012 (5) | −0.0033 (4) | 0.0000 (5) |
C1 | 0.015 (2) | 0.024 (2) | 0.031 (2) | 0.0013 (18) | 0.0042 (18) | −0.0007 (18) |
C2 | 0.017 (3) | 0.031 (2) | 0.029 (2) | 0.0019 (19) | −0.0001 (19) | 0.0019 (19) |
C3 | 0.019 (3) | 0.024 (2) | 0.027 (2) | 0.0019 (18) | 0.0043 (19) | 0.0015 (18) |
C4 | 0.027 (3) | 0.026 (2) | 0.031 (2) | −0.0021 (19) | −0.004 (2) | −0.0017 (19) |
C5 | 0.016 (2) | 0.030 (2) | 0.021 (2) | 0.0036 (18) | 0.0023 (18) | 0.0014 (16) |
C6 | 0.024 (2) | 0.023 (2) | 0.027 (2) | 0.0039 (18) | 0.0051 (19) | 0.0049 (18) |
C7 | 0.021 (2) | 0.027 (2) | 0.023 (2) | 0.0029 (19) | −0.0018 (18) | 0.0015 (17) |
C8 | 0.017 (2) | 0.030 (2) | 0.024 (2) | 0.0011 (18) | −0.0027 (18) | −0.0032 (18) |
C9 | 0.028 (3) | 0.022 (2) | 0.025 (2) | 0.002 (2) | 0.0001 (19) | −0.0019 (17) |
C10 | 0.019 (3) | 0.025 (2) | 0.026 (2) | 0.0030 (18) | −0.0040 (18) | −0.0016 (17) |
Geometric parameters (Å, º) top
O1—N3 | 1.238 (5) | C4—H4A | 0.9600 |
O2—N4 | 1.220 (4) | C4—H4B | 0.9600 |
O3—N4 | 1.227 (5) | C4—H4C | 0.9600 |
N1—C1 | 1.288 (6) | C5—C10 | 1.399 (6) |
N1—C3 | 1.386 (6) | C5—C6 | 1.400 (6) |
N2—N3 | 1.348 (5) | C6—C7 | 1.381 (6) |
N2—C1 | 1.401 (5) | C6—H6 | 0.9300 |
N2—C4 | 1.454 (5) | C7—C8 | 1.376 (6) |
N4—C8 | 1.475 (5) | C7—H7 | 0.9300 |
S1—C2 | 1.720 (5) | C8—C9 | 1.388 (6) |
S1—C1 | 1.730 (4) | C9—C10 | 1.383 (6) |
C2—C3 | 1.359 (6) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C5 | 1.475 (6) | | |
| | | |
C1—N1—C3 | 109.7 (3) | N2—C4—H4C | 109.5 |
N3—N2—C1 | 115.6 (3) | H4A—C4—H4C | 109.5 |
N3—N2—C4 | 121.6 (4) | H4B—C4—H4C | 109.5 |
C1—N2—C4 | 122.8 (3) | C10—C5—C6 | 119.1 (4) |
O1—N3—N2 | 114.0 (3) | C10—C5—C3 | 118.6 (4) |
O2—N4—O3 | 124.0 (4) | C6—C5—C3 | 122.3 (4) |
O2—N4—C8 | 118.5 (4) | C7—C6—C5 | 120.7 (4) |
O3—N4—C8 | 117.5 (4) | C7—C6—H6 | 119.6 |
C2—S1—C1 | 87.7 (2) | C5—C6—H6 | 119.6 |
N1—C1—N2 | 121.2 (4) | C8—C7—C6 | 118.5 (4) |
N1—C1—S1 | 116.8 (4) | C8—C7—H7 | 120.7 |
N2—C1—S1 | 122.0 (3) | C6—C7—H7 | 120.7 |
C3—C2—S1 | 111.0 (4) | C7—C8—C9 | 122.7 (4) |
C3—C2—H2 | 124.5 | C7—C8—N4 | 119.6 (4) |
S1—C2—H2 | 124.5 | C9—C8—N4 | 117.6 (4) |
C2—C3—N1 | 114.8 (4) | C10—C9—C8 | 118.2 (4) |
C2—C3—C5 | 127.4 (4) | C10—C9—H9 | 120.9 |
N1—C3—C5 | 117.8 (3) | C8—C9—H9 | 120.9 |
N2—C4—H4A | 109.5 | C9—C10—C5 | 120.7 (4) |
N2—C4—H4B | 109.5 | C9—C10—H10 | 119.6 |
H4A—C4—H4B | 109.5 | C5—C10—H10 | 119.6 |
| | | |
C1—N2—N3—O1 | −178.1 (4) | C2—C3—C5—C6 | 2.2 (6) |
C4—N2—N3—O1 | −0.9 (6) | N1—C3—C5—C6 | −179.4 (4) |
C3—N1—C1—N2 | −178.9 (3) | C10—C5—C6—C7 | 0.9 (6) |
C3—N1—C1—S1 | 0.8 (5) | C3—C5—C6—C7 | −178.5 (4) |
N3—N2—C1—N1 | −178.8 (4) | C5—C6—C7—C8 | −0.5 (6) |
C4—N2—C1—N1 | 4.1 (6) | C6—C7—C8—C9 | 0.4 (6) |
N3—N2—C1—S1 | 1.6 (5) | C6—C7—C8—N4 | 179.6 (4) |
C4—N2—C1—S1 | −175.6 (4) | O2—N4—C8—C7 | −176.1 (4) |
C2—S1—C1—N1 | −0.1 (4) | O3—N4—C8—C7 | 3.3 (6) |
C2—S1—C1—N2 | 179.5 (4) | O2—N4—C8—C9 | 3.2 (6) |
C1—S1—C2—C3 | −0.6 (4) | O3—N4—C8—C9 | −177.4 (4) |
S1—C2—C3—N1 | 1.2 (5) | C7—C8—C9—C10 | −0.5 (6) |
S1—C2—C3—C5 | 179.7 (3) | N4—C8—C9—C10 | −179.8 (4) |
C1—N1—C3—C2 | −1.3 (5) | C8—C9—C10—C5 | 0.8 (6) |
C1—N1—C3—C5 | −179.9 (4) | C6—C5—C10—C9 | −1.0 (6) |
C2—C3—C5—C10 | −177.2 (4) | C3—C5—C10—C9 | 178.4 (4) |
N1—C3—C5—C10 | 1.2 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.66 | 3.182 (6) | 117 |
C2—H2···N3i | 0.93 | 2.48 | 3.280 (6) | 144 |
C4—H4A···O2ii | 0.96 | 2.60 | 3.525 (5) | 163 |
C4—H4B···O3iii | 0.96 | 2.52 | 3.065 (6) | 116 |
Symmetry codes: (i) x−1, −y+2, z−1/2; (ii) x+1, −y+1, z+1/2; (iii) x+2, y, z+1. |