3,5-Dinitro-benzyl methane-sulfonate.

The title compound, C(8)H(8)N(2)O(7)S, an inter-mediate in the synthesis of N,N-bis-(2-hydroxy-ethyl)-3,5-dinitro-aniline, exists as a discrete mol-ecule; the nitro groups are twisted with respect to the aromatic system [dihedral angles = 17.0 (1) and 26.3 (1)°].

Related literature

For the utility of benzyl methane­sulfonates in synthesis, see: Barker et al. (2008 ▶); Bretonniere et al. (2004 ▶); Oh et al. (2004 ▶); Schirok et al. (2005 ▶). For the incorporation of N,N-bis­(2-hydroxy­ethyl)benzyl­amines in macromolecular metal complexes, see: Crans & Boukhobza (1998 ▶); Koizumi et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

C8H8N2O7S

M = 276.22

Monoclinic,

a = 9.3549 (5) Å

b = 8.7552 (5) Å

c = 14.1526 (8) Å

β = 107.430 (1)°

V = 1105.91 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 89 (1) K

0.32 × 0.14 × 0.14 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.799, T max = 0.971

6374 measured reflections

2233 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.06

2233 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 1995 ▶); cell refinement: SAINT (Bruker, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020850/ng2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020850/ng2470Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8N2O7S	F000 = 568
Mr = 276.22	Dx = 1.659 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4665 reflections
a = 9.3549 (5) Å	θ = 2.3–26.4º
b = 8.7552 (5) Å	µ = 0.32 mm−1
c = 14.1526 (8) Å	T = 89 (1) K
β = 107.430 (1)º	Rod, yellow
V = 1105.91 (11) Å3	0.32 × 0.14 × 0.14 mm
Z = 4

Bruker SMART diffractometer	2233 independent reflections
Radiation source: fine-focus sealed tube	1959 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 89(1) K	θmax = 26.4º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −9→11
Tmin = 0.799, Tmax = 0.971	k = −10→9
6374 measured reflections	l = −17→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.6248P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2233 reflections	Δρmax = 0.28 e Å−3
163 parameters	Δρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S	0.28908 (4)	0.49088 (4)	0.39904 (3)	0.01554 (13)
O1	0.79782 (14)	0.02166 (15)	0.65112 (9)	0.0229 (3)
O2	0.75778 (13)	−0.16192 (14)	0.74420 (9)	0.0199 (3)
O3	0.23786 (14)	−0.34566 (14)	0.65950 (9)	0.0230 (3)
O4	0.06497 (14)	−0.21217 (16)	0.55662 (12)	0.0343 (4)
O5	0.31800 (13)	0.32888 (13)	0.45017 (8)	0.0171 (3)
O6	0.31513 (15)	0.60687 (14)	0.47320 (9)	0.0259 (3)
O7	0.37522 (14)	0.49312 (14)	0.33100 (9)	0.0223 (3)
N1	0.71506 (16)	−0.05791 (16)	0.68364 (10)	0.0166 (3)
N2	0.19482 (16)	−0.23139 (16)	0.60944 (11)	0.0191 (3)
C1	0.35300 (19)	0.15179 (18)	0.58246 (11)	0.0149 (3)
C2	0.50631 (18)	0.11998 (19)	0.61537 (11)	0.0155 (3)
H2A	0.5761	0.1957	0.6155	0.019*
C3	0.55267 (18)	−0.02626 (19)	0.64782 (12)	0.0148 (3)
C4	0.45474 (18)	−0.14488 (18)	0.64856 (11)	0.0148 (3)
H4A	0.4880	−0.2418	0.6720	0.018*
C5	0.30408 (18)	−0.10912 (18)	0.61204 (11)	0.0150 (3)
C6	0.25038 (19)	0.03509 (19)	0.57931 (12)	0.0154 (3)
H6A	0.1479	0.0536	0.5557	0.019*
C7	0.29970 (19)	0.31110 (18)	0.54971 (12)	0.0163 (3)
H7A	0.1955	0.3235	0.5470	0.020*
H7B	0.3593	0.3862	0.5951	0.020*
C8	0.0984 (2)	0.4858 (2)	0.33155 (17)	0.0319 (5)
H8A	0.0702	0.5810	0.2974	0.048*
H8B	0.0399	0.4696	0.3760	0.048*
H8C	0.0807	0.4040	0.2843	0.048*

	U11	U22	U33	U12	U13	U23
S	0.0168 (2)	0.0125 (2)	0.0157 (2)	−0.00083 (14)	0.00236 (16)	0.00293 (14)
O1	0.0180 (6)	0.0286 (7)	0.0219 (7)	−0.0040 (5)	0.0057 (5)	0.0021 (5)
O2	0.0211 (6)	0.0168 (6)	0.0175 (6)	0.0029 (5)	−0.0006 (5)	0.0006 (5)
O3	0.0241 (7)	0.0172 (6)	0.0263 (7)	−0.0011 (5)	0.0057 (5)	0.0086 (5)
O4	0.0164 (7)	0.0248 (7)	0.0529 (9)	−0.0036 (5)	−0.0030 (6)	0.0140 (7)
O5	0.0237 (6)	0.0143 (6)	0.0134 (6)	0.0010 (5)	0.0055 (5)	0.0022 (4)
O6	0.0421 (8)	0.0133 (6)	0.0230 (6)	−0.0022 (5)	0.0105 (6)	0.0000 (5)
O7	0.0250 (7)	0.0227 (7)	0.0200 (6)	−0.0002 (5)	0.0079 (5)	0.0053 (5)
N1	0.0176 (7)	0.0164 (7)	0.0138 (6)	−0.0001 (6)	0.0018 (6)	−0.0035 (6)
N2	0.0189 (7)	0.0149 (7)	0.0227 (7)	−0.0007 (6)	0.0052 (6)	0.0035 (6)
C1	0.0207 (8)	0.0135 (8)	0.0100 (7)	0.0010 (6)	0.0038 (6)	0.0006 (6)
C2	0.0190 (8)	0.0147 (8)	0.0126 (7)	−0.0022 (6)	0.0044 (6)	−0.0009 (6)
C3	0.0155 (8)	0.0178 (8)	0.0099 (7)	0.0001 (6)	0.0018 (6)	−0.0016 (6)
C4	0.0200 (8)	0.0132 (8)	0.0101 (7)	0.0020 (6)	0.0030 (6)	0.0000 (6)
C5	0.0185 (8)	0.0140 (8)	0.0124 (7)	−0.0028 (6)	0.0046 (6)	−0.0004 (6)
C6	0.0171 (8)	0.0163 (8)	0.0120 (7)	0.0010 (6)	0.0031 (6)	0.0005 (6)
C7	0.0216 (8)	0.0136 (8)	0.0136 (8)	−0.0003 (6)	0.0053 (6)	0.0009 (6)
C8	0.0177 (9)	0.0331 (11)	0.0390 (12)	0.0005 (8)	−0.0002 (8)	0.0141 (9)

S—O6	1.4279 (13)	C1—C7	1.507 (2)
S—O7	1.4290 (13)	C2—C3	1.385 (2)
S—O5	1.5783 (12)	C2—H2A	0.9300
S—C8	1.7538 (19)	C3—C4	1.387 (2)
O1—N1	1.2289 (19)	C4—C5	1.384 (2)
O2—N1	1.2322 (18)	C4—H4A	0.9300
O3—N2	1.2223 (18)	C5—C6	1.386 (2)
O4—N2	1.2323 (19)	C6—H6A	0.9300
O5—C7	1.4773 (19)	C7—H7A	0.9700
N1—C3	1.476 (2)	C7—H7B	0.9700
N2—C5	1.473 (2)	C8—H8A	0.9600
C1—C6	1.394 (2)	C8—H8B	0.9600
C1—C2	1.397 (2)	C8—H8C	0.9600
O6—S—O7	118.62 (8)	C5—C4—C3	115.40 (15)
O6—S—O5	109.52 (7)	C5—C4—H4A	122.3
O7—S—O5	105.51 (7)	C3—C4—H4A	122.3
O6—S—C8	109.88 (10)	C4—C5—C6	123.88 (15)
O7—S—C8	108.68 (9)	C4—C5—N2	117.80 (14)
O5—S—C8	103.51 (8)	C6—C5—N2	118.32 (14)
C7—O5—S	118.62 (10)	C5—C6—C1	118.68 (15)
O1—N1—O2	124.75 (14)	C5—C6—H6A	120.7
O1—N1—C3	117.64 (13)	C1—C6—H6A	120.7
O2—N1—C3	117.61 (14)	O5—C7—C1	105.58 (13)
O3—N2—O4	123.85 (14)	O5—C7—H7A	110.6
O3—N2—C5	118.35 (13)	C1—C7—H7A	110.6
O4—N2—C5	117.80 (14)	O5—C7—H7B	110.6
C6—C1—C2	119.55 (15)	C1—C7—H7B	110.6
C6—C1—C7	120.50 (15)	H7A—C7—H7B	108.8
C2—C1—C7	119.95 (15)	S—C8—H8A	109.5
C3—C2—C1	118.88 (15)	S—C8—H8B	109.5
C3—C2—H2A	120.6	H8A—C8—H8B	109.5
C1—C2—H2A	120.6	S—C8—H8C	109.5
C2—C3—C4	123.55 (15)	H8A—C8—H8C	109.5
C2—C3—N1	118.36 (14)	H8B—C8—H8C	109.5
C4—C3—N1	118.09 (14)