Buy article online - an online subscription or single-article purchase is required to access this article.
In the title compound, C
8H
10N
2O
4S, the N—N bond length [1.3488 (18) Å] indicates some double-bond character, while the torsion angle between the aromatic ring and the nitramine group [66.3 (2)°] rules out further delocalization in the molecule. The geometry of the methylsulfonyl substituent is quasi-tetrahedral, as expected. The crystal packing is stabilized by C—H
O hydrogen bonds, with the molecules arranged in chains extended along the [101] direction.
Supporting information
CCDC reference: 274640
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.085
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level A
DIFF020_ALERT_1_A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing
Percentage decrease in standards intensity.
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.80 Ratio
2 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
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
N-Methyl-3-methylsulfonyl-
N-nitroaniline
top
Crystal data top
C8H10N2O4S | F(000) = 960 |
Mr = 230.25 | Dx = 1.580 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5713 reflections |
a = 17.489 (1) Å | θ = 3.1–26.0° |
b = 6.816 (1) Å | µ = 0.33 mm−1 |
c = 16.528 (1) Å | T = 100 K |
β = 100.68 (1)° | Irregular, colourless |
V = 1936.1 (3) Å3 | 0.4 × 0.35 × 0.35 mm |
Z = 8 | |
Data collection top
Oxford Diffraction Xcalibur diffractometer | 1689 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 3.1° |
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1 | h = −20→21 |
ω scans | k = −7→8 |
5713 measured reflections | l = −20→13 |
1920 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0513P)2 + 1.6109P] where P = (Fo2 + 2Fc2)/3 |
1907 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.11104 (2) | 0.25931 (5) | 0.17652 (2) | 0.01260 (14) | |
O1 | 0.08173 (6) | 0.14792 (16) | 0.10310 (6) | 0.0168 (3) | |
O2 | 0.07348 (7) | 0.44256 (17) | 0.18844 (7) | 0.0202 (3) | |
O3 | 0.23882 (7) | −0.00072 (17) | 0.52796 (7) | 0.0209 (3) | |
O4 | 0.20053 (7) | 0.20627 (18) | 0.61338 (7) | 0.0203 (3) | |
N1 | 0.13089 (7) | 0.1734 (2) | 0.48829 (7) | 0.0143 (3) | |
N2 | 0.19313 (8) | 0.1232 (2) | 0.54570 (8) | 0.0157 (3) | |
C1 | 0.10838 (8) | 0.1090 (2) | 0.26339 (9) | 0.0122 (3) | |
C2 | 0.12179 (9) | 0.1982 (2) | 0.34107 (9) | 0.0127 (3) | |
C3 | 0.12014 (9) | 0.0816 (2) | 0.40919 (9) | 0.0129 (3) | |
C4 | 0.10406 (9) | −0.1185 (2) | 0.40114 (10) | 0.0158 (3) | |
C5 | 0.09130 (10) | −0.2034 (2) | 0.32376 (10) | 0.0160 (3) | |
C6 | 0.09414 (9) | −0.0901 (2) | 0.25395 (9) | 0.0138 (3) | |
C7 | 0.21104 (10) | 0.3038 (3) | 0.18096 (10) | 0.0187 (4) | |
C8 | 0.08264 (10) | 0.3355 (3) | 0.50697 (11) | 0.0211 (4) | |
H2 | 0.1314 (10) | 0.336 (3) | 0.3503 (10) | 0.010 (4)* | |
H4 | 0.1025 (12) | −0.194 (3) | 0.4489 (12) | 0.023 (5)* | |
H5 | 0.0783 (10) | −0.334 (3) | 0.3199 (10) | 0.011 (4)* | |
H6 | 0.0885 (10) | −0.148 (3) | 0.2010 (11) | 0.011 (4)* | |
H7A | 0.2331 (12) | 0.351 (3) | 0.2348 (14) | 0.031 (5)* | |
H7B | 0.2163 (13) | 0.401 (3) | 0.1404 (14) | 0.037 (6)* | |
H7C | 0.2367 (13) | 0.185 (3) | 0.1743 (13) | 0.030 (5)* | |
H8A | 0.0395 (11) | 0.343 (3) | 0.4625 (12) | 0.018 (4)* | |
H8B | 0.1142 (14) | 0.453 (4) | 0.5151 (14) | 0.038 (6)* | |
H8C | 0.0671 (13) | 0.311 (3) | 0.5565 (14) | 0.033 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0164 (2) | 0.0134 (2) | 0.0082 (2) | 0.00119 (13) | 0.00270 (14) | 0.00077 (13) |
O1 | 0.0208 (6) | 0.0203 (6) | 0.0088 (5) | 0.0005 (5) | 0.0012 (4) | −0.0014 (4) |
O2 | 0.0310 (7) | 0.0157 (6) | 0.0151 (5) | 0.0071 (5) | 0.0077 (5) | 0.0037 (4) |
O3 | 0.0207 (6) | 0.0227 (6) | 0.0190 (6) | 0.0040 (5) | 0.0026 (5) | 0.0028 (5) |
O4 | 0.0247 (6) | 0.0266 (6) | 0.0085 (5) | −0.0068 (5) | 0.0005 (4) | −0.0023 (5) |
N1 | 0.0186 (7) | 0.0152 (7) | 0.0086 (6) | 0.0016 (5) | 0.0010 (5) | −0.0007 (5) |
N2 | 0.0180 (7) | 0.0179 (7) | 0.0112 (6) | −0.0034 (5) | 0.0027 (5) | 0.0028 (5) |
C1 | 0.0122 (7) | 0.0148 (8) | 0.0100 (7) | 0.0015 (6) | 0.0030 (5) | 0.0008 (6) |
C2 | 0.0146 (7) | 0.0121 (8) | 0.0117 (7) | 0.0005 (6) | 0.0033 (6) | −0.0013 (6) |
C3 | 0.0133 (7) | 0.0145 (7) | 0.0108 (7) | 0.0011 (6) | 0.0022 (5) | −0.0021 (6) |
C4 | 0.0187 (8) | 0.0159 (8) | 0.0133 (7) | 0.0002 (6) | 0.0044 (6) | 0.0044 (6) |
C5 | 0.0197 (8) | 0.0107 (8) | 0.0178 (8) | −0.0009 (6) | 0.0041 (6) | −0.0006 (6) |
C6 | 0.0148 (7) | 0.0141 (8) | 0.0126 (7) | 0.0010 (6) | 0.0029 (6) | −0.0029 (6) |
C7 | 0.0186 (8) | 0.0223 (9) | 0.0151 (8) | −0.0047 (7) | 0.0031 (6) | 0.0014 (7) |
C8 | 0.0229 (9) | 0.0234 (9) | 0.0159 (8) | 0.0061 (7) | 0.0011 (7) | −0.0077 (7) |
Geometric parameters (Å, º) top
S1—O2 | 1.4416 (12) | C3—C4 | 1.394 (2) |
S1—O1 | 1.4426 (11) | C4—C5 | 1.384 (2) |
S1—C7 | 1.7632 (17) | C4—H4 | 0.95 (2) |
S1—C1 | 1.7714 (15) | C5—C6 | 1.397 (2) |
O3—N2 | 1.2349 (17) | C5—H5 | 0.917 (19) |
O4—N2 | 1.2388 (17) | C6—H6 | 0.949 (18) |
N1—N2 | 1.3488 (18) | C7—H7A | 0.96 (2) |
N1—C3 | 1.4298 (19) | C7—H7B | 0.96 (2) |
N1—C8 | 1.458 (2) | C7—H7C | 0.94 (2) |
C1—C6 | 1.383 (2) | C8—H8A | 0.95 (2) |
C1—C2 | 1.400 (2) | C8—H8B | 0.97 (2) |
C2—C3 | 1.383 (2) | C8—H8C | 0.93 (2) |
C2—H2 | 0.960 (18) | | |
| | | |
O2—S1—O1 | 118.10 (7) | C5—C4—C3 | 119.52 (14) |
O2—S1—C7 | 108.59 (8) | C5—C4—H4 | 121.3 (13) |
O1—S1—C7 | 108.70 (8) | C3—C4—H4 | 119.2 (13) |
O2—S1—C1 | 108.02 (7) | C4—C5—C6 | 120.53 (15) |
O1—S1—C1 | 108.59 (7) | C4—C5—H5 | 117.7 (11) |
C7—S1—C1 | 103.93 (8) | C6—C5—H5 | 121.6 (11) |
N2—N1—C3 | 118.99 (12) | C1—C6—C5 | 118.84 (14) |
N2—N1—C8 | 117.81 (12) | C1—C6—H6 | 120.0 (10) |
C3—N1—C8 | 122.82 (12) | C5—C6—H6 | 121.1 (10) |
O3—N2—O4 | 124.27 (13) | S1—C7—H7A | 108.8 (13) |
O3—N2—N1 | 118.66 (12) | S1—C7—H7B | 108.3 (13) |
O4—N2—N1 | 117.07 (13) | H7A—C7—H7B | 109.9 (19) |
C6—C1—C2 | 121.68 (14) | S1—C7—H7C | 109.7 (13) |
C6—C1—S1 | 120.48 (11) | H7A—C7—H7C | 106.3 (18) |
C2—C1—S1 | 117.83 (12) | H7B—C7—H7C | 113.8 (18) |
C3—C2—C1 | 118.17 (14) | N1—C8—H8A | 106.6 (11) |
C3—C2—H2 | 117.5 (10) | N1—C8—H8B | 108.7 (14) |
C1—C2—H2 | 124.3 (10) | H8A—C8—H8B | 114.3 (18) |
C2—C3—C4 | 121.24 (14) | N1—C8—H8C | 109.1 (15) |
C2—C3—N1 | 118.31 (14) | H8A—C8—H8C | 111.8 (18) |
C4—C3—N1 | 120.36 (13) | H8B—C8—H8C | 106 (2) |
| | | |
C3—N1—N2—O3 | −0.1 (2) | C1—C2—C3—C4 | −1.3 (2) |
C8—N1—N2—O3 | −173.12 (14) | C1—C2—C3—N1 | −177.68 (13) |
C3—N1—N2—O4 | 179.84 (13) | N2—N1—C3—C2 | −117.26 (16) |
C8—N1—N2—O4 | 6.8 (2) | C8—N1—C3—C2 | 55.4 (2) |
O2—S1—C1—C6 | 140.40 (13) | N2—N1—C3—C4 | 66.30 (19) |
O1—S1—C1—C6 | 11.20 (15) | C8—N1—C3—C4 | −121.00 (17) |
C7—S1—C1—C6 | −104.39 (14) | C2—C3—C4—C5 | 1.6 (2) |
O2—S1—C1—C2 | −40.17 (13) | N1—C3—C4—C5 | 177.89 (14) |
O1—S1—C1—C2 | −169.37 (11) | C3—C4—C5—C6 | −0.2 (2) |
C7—S1—C1—C2 | 75.04 (13) | C2—C1—C6—C5 | 1.6 (2) |
C6—C1—C2—C3 | −0.3 (2) | S1—C1—C6—C5 | −179.03 (11) |
S1—C1—C2—C3 | −179.72 (11) | C4—C5—C6—C1 | −1.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.949 (18) | 2.577 (17) | 2.9487 (19) | 103.6 (12) |
C7—H7A···O4i | 0.96 (2) | 2.59 (2) | 3.464 (2) | 151.5 (17) |
C8—H8A···O1ii | 0.95 (2) | 2.57 (2) | 3.357 (2) | 140.5 (15) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, y, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.