Buy article online - an online subscription or single-article purchase is required to access this article.
In the crystal structure of the title compound, C6H6N2O4S, the nitro group is nearly coplanar with the aromatic ring, the dihedral angle being 1.6 (2)°. The overall molecular organization is stabilized by well defined intermolecular hydrogen bonds, leading to the formation of an infinite planar network structure.
Supporting information
CCDC reference: 252995
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.112
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 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
0 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4-nitrobenzenesulfonamide
top
Crystal data top
C6H6N2O4S | F(000) = 416 |
Mr = 202.19 | Dx = 1.620 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.068 (1) Å | Cell parameters from 3018 reflections |
b = 13.4916 (18) Å | θ = 1–27.5° |
c = 8.8412 (12) Å | µ = 0.37 mm−1 |
β = 100.459 (3)° | T = 294 K |
V = 829.1 (2) Å3 | Needle, colorless |
Z = 4 | 0.50 × 0.20 × 0.18 mm |
Data collection top
Bruker CCD Area Detector diffractometer | 1901 independent reflections |
Radiation source: fine-focus sealed tube | 1457 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 27.6°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick 1996) | h = −9→8 |
Tmin = 0.835, Tmax = 0.936 | k = −17→17 |
5526 measured reflections | l = −11→9 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0616P)2 + 0.1102P] where P = (Fo2 + 2Fc2)/3 |
1901 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.46 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 | 0.60605 (7) | 0.27053 (4) | 0.43746 (5) | 0.03494 (18) | |
O1 | 0.4700 (2) | 0.23727 (12) | 0.30737 (17) | 0.0532 (4) | |
O2 | 0.7726 (2) | 0.32344 (10) | 0.41461 (16) | 0.0459 (4) | |
O3 | −0.0009 (3) | 0.52422 (13) | 0.7774 (2) | 0.0656 (5) | |
O4 | 0.2647 (3) | 0.57388 (14) | 0.91418 (19) | 0.0683 (5) | |
N1 | 0.6819 (3) | 0.17452 (12) | 0.5386 (2) | 0.0468 (5) | |
H1A | 0.5923 | 0.1366 | 0.5708 | 0.056* | |
H1B | 0.7737 | 0.1936 | 0.6175 | 0.056* | |
N2 | 0.1748 (3) | 0.52473 (13) | 0.8104 (2) | 0.0466 (5) | |
C1 | 0.4785 (3) | 0.34619 (13) | 0.5482 (2) | 0.0325 (4) | |
C2 | 0.5796 (3) | 0.40450 (15) | 0.6644 (2) | 0.0418 (5) | |
H2 | 0.7134 | 0.4042 | 0.6838 | 0.050* | |
C3 | 0.4800 (3) | 0.46312 (15) | 0.7513 (2) | 0.0431 (5) | |
H3 | 0.5452 | 0.5023 | 0.8305 | 0.052* | |
C4 | 0.2824 (3) | 0.46234 (13) | 0.7181 (2) | 0.0356 (4) | |
C5 | 0.1795 (3) | 0.40530 (15) | 0.6039 (2) | 0.0422 (5) | |
H5 | 0.0457 | 0.4066 | 0.5847 | 0.051* | |
C6 | 0.2789 (3) | 0.34569 (15) | 0.5177 (2) | 0.0410 (5) | |
H6 | 0.2126 | 0.3057 | 0.4401 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0356 (3) | 0.0358 (3) | 0.0335 (3) | −0.00188 (19) | 0.0066 (2) | −0.00139 (19) |
O1 | 0.0486 (10) | 0.0678 (10) | 0.0410 (9) | −0.0001 (8) | 0.0023 (7) | −0.0188 (7) |
O2 | 0.0450 (9) | 0.0452 (8) | 0.0505 (9) | −0.0050 (7) | 0.0167 (7) | 0.0041 (7) |
O3 | 0.0524 (11) | 0.0647 (11) | 0.0860 (13) | 0.0057 (9) | 0.0290 (10) | −0.0130 (9) |
O4 | 0.0866 (14) | 0.0706 (11) | 0.0447 (10) | 0.0201 (10) | 0.0037 (9) | −0.0175 (9) |
N1 | 0.0553 (12) | 0.0348 (9) | 0.0519 (11) | 0.0018 (8) | 0.0142 (9) | 0.0052 (8) |
N2 | 0.0615 (13) | 0.0405 (10) | 0.0399 (10) | 0.0088 (9) | 0.0144 (9) | 0.0044 (8) |
C1 | 0.0340 (10) | 0.0311 (9) | 0.0315 (10) | −0.0009 (8) | 0.0037 (7) | 0.0001 (7) |
C2 | 0.0310 (10) | 0.0449 (11) | 0.0453 (12) | 0.0014 (9) | −0.0038 (9) | −0.0066 (9) |
C3 | 0.0457 (12) | 0.0433 (11) | 0.0365 (11) | −0.0002 (9) | −0.0026 (9) | −0.0083 (9) |
C4 | 0.0421 (11) | 0.0333 (10) | 0.0325 (10) | 0.0033 (8) | 0.0093 (8) | 0.0042 (7) |
C5 | 0.0311 (10) | 0.0497 (12) | 0.0464 (12) | −0.0024 (9) | 0.0082 (9) | −0.0020 (9) |
C6 | 0.0349 (11) | 0.0448 (11) | 0.0422 (11) | −0.0067 (9) | 0.0043 (9) | −0.0087 (9) |
Geometric parameters (Å, º) top
S1—O2 | 1.4223 (14) | C1—C6 | 1.387 (3) |
S1—O1 | 1.4310 (15) | C2—C3 | 1.381 (3) |
S1—N1 | 1.6094 (17) | C2—H2 | 0.93 |
S1—C1 | 1.7700 (19) | C3—C4 | 1.374 (3) |
O3—N2 | 1.224 (2) | C3—H3 | 0.93 |
O4—N2 | 1.214 (2) | C4—C5 | 1.369 (3) |
N1—H1A | 0.90 | C5—C6 | 1.385 (3) |
N1—H1B | 0.90 | C5—H5 | 0.93 |
N2—C4 | 1.476 (3) | C6—H6 | 0.93 |
C1—C2 | 1.386 (3) | | |
| | | |
O2—S1—O1 | 119.75 (10) | C3—C2—C1 | 119.42 (19) |
O2—S1—N1 | 106.38 (9) | C3—C2—H2 | 120.3 |
O1—S1—N1 | 107.55 (10) | C1—C2—H2 | 120.3 |
O2—S1—C1 | 107.88 (9) | C4—C3—C2 | 118.54 (18) |
O1—S1—C1 | 106.84 (9) | C4—C3—H3 | 120.7 |
N1—S1—C1 | 107.99 (9) | C2—C3—H3 | 120.7 |
S1—N1—H1A | 116.8 | C5—C4—C3 | 123.08 (18) |
S1—N1—H1B | 108.7 | C5—C4—N2 | 118.04 (19) |
H1A—N1—H1B | 111.5 | C3—C4—N2 | 118.88 (18) |
O4—N2—O3 | 123.55 (19) | C4—C5—C6 | 118.51 (19) |
O4—N2—C4 | 118.57 (19) | C4—C5—H5 | 120.7 |
O3—N2—C4 | 117.87 (18) | C6—C5—H5 | 120.7 |
C2—C1—C6 | 121.09 (18) | C5—C6—C1 | 119.36 (18) |
C2—C1—S1 | 119.45 (15) | C5—C6—H6 | 120.3 |
C6—C1—S1 | 119.46 (14) | C1—C6—H6 | 120.3 |
| | | |
O2—S1—C1—C2 | −37.29 (18) | C2—C3—C4—N2 | 179.95 (17) |
O1—S1—C1—C2 | −167.26 (15) | O4—N2—C4—C5 | 178.36 (19) |
N1—S1—C1—C2 | 77.31 (17) | O3—N2—C4—C5 | −1.9 (3) |
O2—S1—C1—C6 | 143.09 (16) | O4—N2—C4—C3 | −0.9 (3) |
O1—S1—C1—C6 | 13.12 (19) | O3—N2—C4—C3 | 178.84 (19) |
N1—S1—C1—C6 | −102.31 (17) | C3—C4—C5—C6 | −0.1 (3) |
C6—C1—C2—C3 | 0.0 (3) | N2—C4—C5—C6 | −179.31 (17) |
S1—C1—C2—C3 | −179.66 (16) | C4—C5—C6—C1 | −0.6 (3) |
C1—C2—C3—C4 | −0.7 (3) | C2—C1—C6—C5 | 0.7 (3) |
C2—C3—C4—C5 | 0.7 (3) | S1—C1—C6—C5 | −179.68 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.90 | 2.20 | 3.025 (2) | 153 |
N1—H1B···O1ii | 0.90 | 2.18 | 3.075 (3) | 171 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, 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.