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In the title molecule, C
12H
8N
2O
7S, there are weak C-H
O interactions which generate rings of motifs
S(5),
R21(5),
R12(4) and
R12(8).
Supporting information
CCDC reference: 222904
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.070
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - N1 = 5.66 su
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.11
From the CIF: _reflns_number_total 2832
Count of symmetry unique reflns 1602
Completeness (_total/calc) 176.78%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1230
Fraction of Friedel pairs measured 0.768
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
3-Nitrobenzenesulfonyl chloride (4.9 mmol) dissolved in acetone (5 ml) was added to 2-nitrophenol (5.0 mmol) in NaOH (4 ml, 5%) and shaken well. The crude title compound (2.6 mmol, yield: 53%) was precipitated from solution. Diffraction quality crystals were obtained by recrystallizing the crude product from aqueous ethanol.
All H atoms were located from difference Fourier maps and their positional parameters were refined, with Uiso = 1.2Ueq(parent atom). The C—H bond lengths are in the range 0.91 (2)–1.03 (2) Å.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2-Nitrophenyl 3-nitrobenzenesulfonate
top
Crystal data top
C12H8N2O7S | Dx = 1.654 Mg m−3 |
Mr = 324.26 | Melting point = 358–360 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2719 reflections |
a = 19.9671 (8) Å | θ = 2.6–26.7° |
b = 12.7083 (5) Å | µ = 0.29 mm−1 |
c = 5.1306 (2) Å | T = 120 K |
V = 1301.88 (9) Å3 | Block, colourless |
Z = 4 | 0.14 × 0.12 × 0.08 mm |
F(000) = 664 | |
Data collection top
Bruker SMART CCD 6K area-detector diffractometer | 2355 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 27.1°, θmin = 1.9° |
Detector resolution: 8 pixels mm-1 | h = −24→25 |
ω scans | k = −16→15 |
9331 measured reflections | l = −6→6 |
2832 independent reflections | |
Refinement top
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)] = 0.034 | Only H-atom coordinates refined |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
2832 reflections | Δρmax = 0.18 e Å−3 |
223 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983), 1230 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.10 (7) |
Crystal data top
C12H8N2O7S | V = 1301.88 (9) Å3 |
Mr = 324.26 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 19.9671 (8) Å | µ = 0.29 mm−1 |
b = 12.7083 (5) Å | T = 120 K |
c = 5.1306 (2) Å | 0.14 × 0.12 × 0.08 mm |
Data collection top
Bruker SMART CCD 6K area-detector diffractometer | 2355 reflections with I > 2σ(I) |
9331 measured reflections | Rint = 0.059 |
2832 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | Only H-atom coordinates refined |
wR(F2) = 0.070 | Δρmax = 0.18 e Å−3 |
S = 0.96 | Δρmin = −0.33 e Å−3 |
2832 reflections | Absolute structure: (Flack, 1983), 1230 Friedel pairs |
223 parameters | Absolute structure parameter: −0.10 (7) |
1 restraint | |
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 | |
C1 | 0.10099 (11) | 0.59508 (17) | 0.7938 (5) | 0.0226 (5) | |
C2 | 0.09759 (12) | 0.68560 (18) | 0.6474 (5) | 0.0263 (5) | |
H2 | 0.0626 (12) | 0.7325 (19) | 0.674 (5) | 0.032* | |
C3 | 0.14536 (12) | 0.70336 (18) | 0.4570 (5) | 0.0290 (6) | |
H3 | 0.1449 (12) | 0.7663 (19) | 0.347 (5) | 0.035* | |
C4 | 0.19539 (12) | 0.62919 (18) | 0.4122 (5) | 0.0270 (5) | |
H4 | 0.2278 (12) | 0.6363 (19) | 0.279 (5) | 0.032* | |
C5 | 0.19640 (10) | 0.53812 (16) | 0.5619 (4) | 0.0219 (5) | |
C6 | 0.14998 (10) | 0.51890 (17) | 0.7576 (4) | 0.0210 (5) | |
H6 | 0.1521 (11) | 0.4514 (17) | 0.869 (5) | 0.025* | |
C7 | 0.35510 (10) | 0.57182 (16) | 0.6233 (4) | 0.0206 (5) | |
C8 | 0.34033 (11) | 0.66443 (18) | 0.7508 (5) | 0.0253 (5) | |
H8 | 0.3064 (12) | 0.6656 (17) | 0.885 (5) | 0.030* | |
C9 | 0.37541 (11) | 0.75507 (18) | 0.6868 (5) | 0.0275 (5) | |
H9 | 0.3655 (12) | 0.818 (2) | 0.779 (5) | 0.033* | |
C10 | 0.42276 (10) | 0.75352 (17) | 0.4901 (6) | 0.0258 (5) | |
H10 | 0.4449 (11) | 0.8149 (19) | 0.441 (5) | 0.031* | |
C11 | 0.43749 (11) | 0.66092 (18) | 0.3604 (5) | 0.0239 (5) | |
H11 | 0.4698 (12) | 0.6597 (17) | 0.235 (5) | 0.029* | |
C12 | 0.40411 (10) | 0.57001 (16) | 0.4328 (4) | 0.0204 (5) | |
S1 | 0.25954 (2) | 0.44364 (4) | 0.50573 (12) | 0.02233 (12) | |
O1 | 0.00775 (8) | 0.64556 (11) | 1.0301 (4) | 0.0348 (4) | |
O2 | 0.05613 (8) | 0.49898 (12) | 1.1363 (3) | 0.0321 (4) | |
O3 | 0.28079 (8) | 0.45294 (12) | 0.2416 (3) | 0.0293 (4) | |
O4 | 0.24002 (7) | 0.34518 (12) | 0.6120 (3) | 0.0277 (4) | |
O5 | 0.31924 (7) | 0.48061 (11) | 0.6923 (3) | 0.0225 (3) | |
O6 | 0.42793 (8) | 0.39240 (12) | 0.4488 (3) | 0.0332 (4) | |
O7 | 0.44083 (8) | 0.47339 (13) | 0.0786 (3) | 0.0340 (4) | |
N1 | 0.05125 (8) | 0.57834 (14) | 1.0011 (4) | 0.0261 (4) | |
N2 | 0.42532 (8) | 0.47095 (15) | 0.3104 (4) | 0.0247 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0213 (11) | 0.0237 (12) | 0.0229 (12) | −0.0054 (9) | 0.0008 (10) | −0.0047 (9) |
C2 | 0.0271 (11) | 0.0213 (12) | 0.0305 (14) | 0.0014 (9) | −0.0046 (11) | −0.0024 (10) |
C3 | 0.0331 (12) | 0.0222 (12) | 0.0318 (16) | −0.0029 (9) | −0.0016 (12) | 0.0047 (10) |
C4 | 0.0262 (12) | 0.0313 (13) | 0.0234 (12) | −0.0065 (10) | 0.0001 (10) | 0.0051 (10) |
C5 | 0.0212 (10) | 0.0217 (11) | 0.0228 (13) | −0.0018 (8) | −0.0046 (9) | −0.0016 (8) |
C6 | 0.0213 (10) | 0.0197 (11) | 0.0220 (12) | −0.0034 (8) | −0.0028 (10) | −0.0009 (10) |
C7 | 0.0185 (10) | 0.0243 (12) | 0.0189 (11) | −0.0011 (8) | −0.0050 (9) | 0.0040 (9) |
C8 | 0.0224 (11) | 0.0319 (14) | 0.0216 (12) | 0.0006 (9) | 0.0045 (10) | −0.0012 (10) |
C9 | 0.0282 (11) | 0.0240 (12) | 0.0303 (13) | 0.0016 (9) | 0.0005 (11) | −0.0061 (11) |
C10 | 0.0212 (10) | 0.0236 (11) | 0.0326 (12) | −0.0023 (8) | −0.0002 (12) | 0.0022 (12) |
C11 | 0.0201 (11) | 0.0285 (13) | 0.0231 (12) | 0.0020 (9) | 0.0036 (10) | 0.0022 (10) |
C12 | 0.0187 (10) | 0.0217 (11) | 0.0207 (13) | 0.0042 (8) | −0.0020 (9) | −0.0016 (8) |
S1 | 0.0208 (2) | 0.0247 (3) | 0.0215 (2) | −0.0013 (2) | 0.0002 (3) | −0.0018 (3) |
O1 | 0.0314 (8) | 0.0342 (9) | 0.0389 (10) | 0.0074 (7) | 0.0056 (9) | −0.0076 (9) |
O2 | 0.0351 (9) | 0.0296 (9) | 0.0318 (9) | −0.0017 (7) | 0.0097 (8) | 0.0048 (8) |
O3 | 0.0267 (8) | 0.0404 (10) | 0.0209 (9) | −0.0005 (7) | 0.0009 (7) | −0.0045 (7) |
O4 | 0.0265 (8) | 0.0225 (8) | 0.0340 (9) | −0.0003 (6) | 0.0003 (8) | −0.0024 (6) |
O5 | 0.0226 (7) | 0.0242 (8) | 0.0205 (8) | −0.0044 (6) | −0.0010 (7) | 0.0030 (6) |
O6 | 0.0344 (9) | 0.0207 (8) | 0.0444 (13) | 0.0043 (6) | −0.0065 (8) | −0.0020 (8) |
O7 | 0.0285 (9) | 0.0438 (10) | 0.0299 (11) | 0.0031 (7) | 0.0064 (8) | −0.0103 (8) |
N1 | 0.0269 (9) | 0.0273 (10) | 0.0241 (9) | −0.0020 (7) | 0.0010 (11) | −0.0083 (10) |
N2 | 0.0165 (9) | 0.0264 (11) | 0.0313 (12) | 0.0000 (7) | 0.0003 (9) | −0.0070 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (3) | C8—H8 | 0.97 (2) |
C1—C6 | 1.389 (3) | C9—C10 | 1.383 (3) |
C1—N1 | 1.471 (3) | C9—H9 | 0.95 (3) |
C2—C3 | 1.384 (3) | C10—C11 | 1.383 (3) |
C2—H2 | 0.93 (2) | C10—H10 | 0.93 (2) |
C3—C4 | 1.393 (3) | C11—C12 | 1.384 (3) |
C3—H3 | 0.98 (3) | C11—H11 | 0.91 (2) |
C4—C5 | 1.389 (3) | C12—N2 | 1.469 (3) |
C4—H4 | 0.94 (3) | S1—O4 | 1.4195 (16) |
C5—C6 | 1.388 (3) | S1—O3 | 1.4250 (16) |
C5—S1 | 1.765 (2) | S1—O5 | 1.5992 (16) |
C6—H6 | 1.03 (2) | O1—N1 | 1.227 (2) |
C7—C8 | 1.378 (3) | O2—N1 | 1.228 (2) |
C7—C12 | 1.383 (3) | O6—N2 | 1.226 (2) |
C7—O5 | 1.408 (2) | O7—N2 | 1.229 (3) |
C8—C9 | 1.388 (3) | | |
| | | |
C2—C1—C6 | 123.0 (2) | C10—C9—H9 | 121.2 (15) |
C2—C1—N1 | 118.9 (2) | C8—C9—H9 | 118.4 (15) |
C6—C1—N1 | 118.13 (19) | C9—C10—C11 | 120.5 (2) |
C1—C2—C3 | 119.2 (2) | C9—C10—H10 | 120.6 (15) |
C1—C2—H2 | 119.6 (16) | C11—C10—H10 | 118.9 (15) |
C3—C2—H2 | 121.2 (16) | C10—C11—C12 | 118.6 (2) |
C2—C3—C4 | 120.0 (2) | C10—C11—H11 | 120.3 (15) |
C2—C3—H3 | 122.3 (15) | C12—C11—H11 | 121.0 (14) |
C4—C3—H3 | 117.7 (15) | C7—C12—C11 | 121.07 (19) |
C5—C4—C3 | 118.9 (2) | C7—C12—N2 | 121.34 (18) |
C5—C4—H4 | 117.9 (15) | C11—C12—N2 | 117.49 (19) |
C3—C4—H4 | 123.1 (15) | O4—S1—O3 | 121.34 (10) |
C6—C5—C4 | 122.5 (2) | O4—S1—O5 | 103.53 (9) |
C6—C5—S1 | 118.39 (16) | O3—S1—O5 | 108.83 (9) |
C4—C5—S1 | 119.14 (17) | O4—S1—C5 | 109.93 (9) |
C5—C6—C1 | 116.4 (2) | O3—S1—C5 | 108.15 (10) |
C5—C6—H6 | 121.3 (13) | O5—S1—C5 | 103.59 (9) |
C1—C6—H6 | 122.3 (13) | C7—O5—S1 | 118.08 (13) |
C8—C7—C12 | 120.06 (19) | O1—N1—O2 | 124.0 (2) |
C8—C7—O5 | 118.36 (19) | O1—N1—C1 | 117.7 (2) |
C12—C7—O5 | 121.58 (18) | O2—N1—C1 | 118.28 (16) |
C7—C8—C9 | 119.2 (2) | O6—N2—O7 | 124.76 (19) |
C7—C8—H8 | 120.1 (14) | O6—N2—C12 | 117.54 (18) |
C9—C8—H8 | 120.7 (14) | O7—N2—C12 | 117.67 (19) |
C10—C9—C8 | 120.4 (2) | | |
| | | |
C6—C1—C2—C3 | −0.9 (3) | C10—C11—C12—N2 | −174.1 (2) |
N1—C1—C2—C3 | 178.1 (2) | C6—C5—S1—O4 | 19.79 (19) |
C1—C2—C3—C4 | 1.2 (3) | C4—C5—S1—O4 | −161.09 (17) |
C2—C3—C4—C5 | −0.2 (3) | C6—C5—S1—O3 | 154.30 (16) |
C3—C4—C5—C6 | −1.1 (3) | C4—C5—S1—O3 | −26.6 (2) |
C3—C4—C5—S1 | 179.86 (18) | C6—C5—S1—O5 | −90.30 (17) |
C4—C5—C6—C1 | 1.3 (3) | C4—C5—S1—O5 | 88.81 (18) |
S1—C5—C6—C1 | −179.63 (16) | C8—C7—O5—S1 | 101.3 (2) |
C2—C1—C6—C5 | −0.3 (3) | C12—C7—O5—S1 | −78.7 (2) |
N1—C1—C6—C5 | −179.35 (18) | O4—S1—O5—C7 | 173.34 (15) |
C12—C7—C8—C9 | −0.4 (3) | O3—S1—O5—C7 | 43.00 (16) |
O5—C7—C8—C9 | 179.6 (2) | C5—S1—O5—C7 | −71.90 (16) |
C7—C8—C9—C10 | 2.6 (3) | C2—C1—N1—O1 | 1.6 (3) |
C8—C9—C10—C11 | −2.2 (4) | C6—C1—N1—O1 | −179.3 (2) |
C9—C10—C11—C12 | −0.3 (4) | C2—C1—N1—O2 | −177.6 (2) |
C8—C7—C12—C11 | −2.2 (3) | C6—C1—N1—O2 | 1.5 (3) |
O5—C7—C12—C11 | 177.80 (19) | C7—C12—N2—O6 | −36.8 (3) |
C8—C7—C12—N2 | 174.3 (2) | C11—C12—N2—O6 | 139.80 (19) |
O5—C7—C12—N2 | −5.7 (3) | C7—C12—N2—O7 | 145.0 (2) |
C10—C11—C12—C7 | 2.5 (3) | C11—C12—N2—O7 | −38.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 (2) | 2.40 (3) | 2.708 (3) | 99.2 (18) |
C4—H4···O3 | 0.94 (3) | 2.57 (2) | 2.948 (3) | 104.5 (17) |
C6—H6···O2 | 1.03 (2) | 2.43 (2) | 2.711 (3) | 94.2 (14) |
C6—H6···O4 | 1.03 (2) | 2.58 (2) | 2.944 (3) | 100.4 (16) |
C11—H11···O7 | 0.91 (2) | 2.57 (2) | 2.788 (3) | 94.4 (16) |
C8—H8···O4i | 0.97 (2) | 2.72 (2) | 3.359 (3) | 123.8 (17) |
C9—H9···O4i | 0.95 (3) | 2.73 (3) | 3.374 (3) | 125.3 (18) |
C2—H2···O6i | 0.93 (2) | 2.48 (2) | 3.092 (3) | 123.5 (18) |
C3—H3···O6ii | 0.98 (3) | 2.98 (3) | 3.836 (3) | 147.1 (19) |
C3—H3···O4ii | 0.98 (3) | 2.78 (3) | 3.409 (3) | 122.5 (18) |
C9—H9···O2ii | 0.95 (3) | 2.88 (2) | 3.398 (3) | 115.6 (18) |
C4—H4···O4ii | 0.94 (3) | 2.86 (2) | 3.401 (3) | 117.3 (18) |
C10—H10···O2ii | 0.93 (2) | 2.54 (2) | 3.236 (3) | 131.4 (18) |
C3—H3···O5ii | 0.98 (3) | 2.93 (2) | 3.842 (3) | 156 (2) |
C10—H10···O1iii | 0.93 (2) | 2.51 (2) | 3.177 (3) | 129.2 (19) |
C11—H11···O1iii | 0.91 (2) | 2.79 (2) | 3.300 (3) | 116.2 (17) |
C11—H11···O6iv | 0.91 (2) | 2.60 (2) | 3.484 (3) | 163.5 (19) |
Symmetry codes: (i) −x+1/2, y+1/2, z+1/2; (ii) −x+1/2, y+1/2, z−1/2; (iii) x+1/2, −y+3/2, z−1; (iv) −x+1, −y+1, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C12H8N2O7S |
Mr | 324.26 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 120 |
a, b, c (Å) | 19.9671 (8), 12.7083 (5), 5.1306 (2) |
V (Å3) | 1301.88 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.14 × 0.12 × 0.08 |
|
Data collection |
Diffractometer | Bruker SMART CCD 6K area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9331, 2832, 2355 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.641 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.070, 0.96 |
No. of reflections | 2832 |
No. of parameters | 223 |
No. of restraints | 1 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.18, −0.33 |
Absolute structure | (Flack, 1983), 1230 Friedel pairs |
Absolute structure parameter | −0.10 (7) |
Selected geometric parameters (Å, º) topC1—N1 | 1.471 (3) | S1—O5 | 1.5992 (16) |
C5—S1 | 1.765 (2) | O1—N1 | 1.227 (2) |
C7—O5 | 1.408 (2) | O2—N1 | 1.228 (2) |
C12—N2 | 1.469 (3) | O6—N2 | 1.226 (2) |
S1—O4 | 1.4195 (16) | O7—N2 | 1.229 (3) |
S1—O3 | 1.4250 (16) | | |
| | | |
O4—S1—O3 | 121.34 (10) | O1—N1—O2 | 124.0 (2) |
O4—S1—O5 | 103.53 (9) | O1—N1—C1 | 117.7 (2) |
O3—S1—O5 | 108.83 (9) | O2—N1—C1 | 118.28 (16) |
O4—S1—C5 | 109.93 (9) | O6—N2—O7 | 124.76 (19) |
O3—S1—C5 | 108.15 (10) | O6—N2—C12 | 117.54 (18) |
O5—S1—C5 | 103.59 (9) | O7—N2—C12 | 117.67 (19) |
C7—O5—S1 | 118.08 (13) | | |
| | | |
C5—S1—O5—C7 | −71.90 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 (2) | 2.40 (3) | 2.708 (3) | 99.2 (18) |
C4—H4···O3 | 0.94 (3) | 2.57 (2) | 2.948 (3) | 104.5 (17) |
C6—H6···O2 | 1.03 (2) | 2.43 (2) | 2.711 (3) | 94.2 (14) |
C6—H6···O4 | 1.03 (2) | 2.58 (2) | 2.944 (3) | 100.4 (16) |
C11—H11···O7 | 0.91 (2) | 2.57 (2) | 2.788 (3) | 94.4 (16) |
C8—H8···O4i | 0.97 (2) | 2.72 (2) | 3.359 (3) | 123.8 (17) |
C9—H9···O4i | 0.95 (3) | 2.73 (3) | 3.374 (3) | 125.3 (18) |
C2—H2···O6i | 0.93 (2) | 2.48 (2) | 3.092 (3) | 123.5 (18) |
C3—H3···O6ii | 0.98 (3) | 2.98 (3) | 3.836 (3) | 147.1 (19) |
C3—H3···O4ii | 0.98 (3) | 2.78 (3) | 3.409 (3) | 122.5 (18) |
C9—H9···O2ii | 0.95 (3) | 2.88 (2) | 3.398 (3) | 115.6 (18) |
C4—H4···O4ii | 0.94 (3) | 2.86 (2) | 3.401 (3) | 117.3 (18) |
C10—H10···O2ii | 0.93 (2) | 2.54 (2) | 3.236 (3) | 131.4 (18) |
C3—H3···O5ii | 0.98 (3) | 2.93 (2) | 3.842 (3) | 156 (2) |
C10—H10···O1iii | 0.93 (2) | 2.51 (2) | 3.177 (3) | 129.2 (19) |
C11—H11···O1iii | 0.91 (2) | 2.79 (2) | 3.300 (3) | 116.2 (17) |
C11—H11···O6iv | 0.91 (2) | 2.60 (2) | 3.484 (3) | 163.5 (19) |
Symmetry codes: (i) −x+1/2, y+1/2, z+1/2; (ii) −x+1/2, y+1/2, z−1/2; (iii) x+1/2, −y+3/2, z−1; (iv) −x+1, −y+1, z−1/2. |
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Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989) and in many other fields (Spungin et al., 1992; Tharakan et al., 1992; Alford et al., 1991; Jiang et al., 1990; Narayanan & Krakow, 1983). The molecular and crystal structure of 3-nitrobenzenesulfonyl chloride has been recently reported (Vembu, Nallu, Spencer & Howard, 2003c). In view of the biological importance of its analogues and also to comapre its structural parameters with those of its precursor, 3-nitrobenzenesulfonyl chloride, an X-ray study of the title compound, (I), was undertaken.
The molecular structure of (I) shown in Fig. 1 and selected geometric parameters are given in Table 1. Atoms N1, O1 and O2 deviate from the mean plane formed by atoms C1–C6 by 0.031 (3), 0.015 (4) and 0.085 (4) Å, respectively. Atoms N2, O6, O7 deviate from the mean plane formed by atoms C7–C12 by 0.146 (3), 0.874 (4) and −0.456 (4) Å, respectively. The dihedral angle between the abovementioned planes is 39.68 (8)°. This shows their non-coplanar orientation, similar to that reported for other aromatic sulfonates (Vembu, Nallu, Garrison & Youngs, 2003b,c,d,e; Vembu, Nallu, Spencer & Howard, 2003a,b,d,e), and in contrast to the near coplanar orientation found in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003a) and 4-methoxyphenyl 4-toluenesulfonate (Vembu, Nallu, Garrison, Hindi & Youngs, 2003).
The crystal structure is stabilized by weak C—H···O interactions (Table 2). The range of H···O distances found in (I) agrees with that found for weak C—H···O bonds (Desiraju & Steiner, 1999). As shown in Fig. 2, each of the C2—H2···O1, C4—H4···O3, C6—H6···O2, C6—H6···O4 and C11—H11···O7 interactions generates a S(5) graph-set motif (Bernstein et al., 1995; Etter, 1990). The C6—H6···O2 and C6—H6···O4 interactions constitute a pair of bifurcated donor bonds. As seen in Fig. 3, the C8—H8···O4i and C9—H9···O4i interactions constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C3—H3···O6ii and C3—H3···O4ii interactions constitute a pair of bifurcated donor bonds generating an R12(8) motif. The C3—H3···O4ii and C4—H4···O4ii interactions constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C3—H3···O4ii and C3—H3···O5ii interactions constitute a pair of bifurcated donor bonds generating a symmetrical hydrogen-bonded chelate motif of graph-set R12(4). The C9—H9···O2ii and C10—H10···O2ii interactions together form a pair of bifurcated acceptor bonds generating an R21(5) motif. The C10—H10···O1iii and C11—H11···O1iii interactions together constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C2—H2···O6i and C11—H11···O6iv interactions also contribute for the supramolecular aggregation of the title compound (Fig. 4).