N-Meth­yl-3-methyl­sulfon­yl-N-nitro­aniline

In the title compound, C₈H₁₀N₂O₄S, 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.4 × 0.35 × 0.35 mm
Z = 8

Data collection

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

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 1.6109P] where P = (Fo^2 + 2Fc^2)/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

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	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O4^i	0.96 (2)	2.59 (2)	3.464 (2)	151.5 (17)
C8—H8A···O1^ii	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.