In the title molecule, C
12H
7N
3O
9S, there are weak C-H
O interactions which generate rings of motifs
S(5),
R12(8) and
R12(4).
Supporting information
CCDC reference: 222903
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.059
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O8 .. N1 = 2.82 Ang.
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N1 = 6.79 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O8 - N3 = 5.12 su
PLAT350_ALERT_3_C Short C-H Bond (0.96A) C8 - H8 = 0.81 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C8 = 3.01 Ang.
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 2952
Count of symmetry unique reflns 1644
Completeness (_total/calc) 179.56%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1308
Fraction of Friedel pairs measured 0.796
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 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
4 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
1 ALERT type 4 Improvement, methodology, query or suggestion
2,4-Dinitrophenol (5 mmol) and triethylamine (5 mmol) were dissolved in acetone (20 ml). To this solution, 3-nitrobenzenesulfonyl chloride (5 mmol) in acetone (20 ml) was added. The resulting solution was allowed to evaporate. The residue was washed several times with aqueous triethylamine solution. The crude product of the title compound, (I), was recrystallized from a 1:1 mixture of petroleum ether and 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 0.81 (2)–0.97 (2) Å.
Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (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.
2,4-Dinitrophenyl 3-nitrobenzenesulfonate
top
Crystal data top
C12H7N3O9S | Dx = 1.732 Mg m−3 |
Mr = 369.27 | Melting point = 377–379 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3073 reflections |
a = 27.730 (2) Å | θ = 2.4–27.1° |
b = 4.7374 (3) Å | µ = 0.29 mm−1 |
c = 10.7800 (8) Å | T = 120 K |
V = 1416.16 (17) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.25 × 0.11 mm |
F(000) = 752 | |
Data collection top
Bruker SMART CCD 6K area-detector diffractometer | 2619 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.1°, θmin = 2.9° |
Detector resolution: 8 pixels mm-1 | h = −35→27 |
ω scans | k = −6→5 |
8989 measured reflections | l = −13→12 |
2952 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)] = 0.030 | Only H-atom coordinates refined |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0274P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
2952 reflections | Δρmax = 0.34 e Å−3 |
247 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983); 1310 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (6) |
Crystal data top
C12H7N3O9S | V = 1416.16 (17) Å3 |
Mr = 369.27 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 27.730 (2) Å | µ = 0.29 mm−1 |
b = 4.7374 (3) Å | T = 120 K |
c = 10.7800 (8) Å | 0.28 × 0.25 × 0.11 mm |
Data collection top
Bruker SMART CCD 6K area-detector diffractometer | 2619 reflections with I > 2σ(I) |
8989 measured reflections | Rint = 0.033 |
2952 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | Only H-atom coordinates refined |
wR(F2) = 0.059 | Δρmax = 0.34 e Å−3 |
S = 0.97 | Δρmin = −0.33 e Å−3 |
2952 reflections | Absolute structure: (Flack, 1983); 1310 Friedel pairs |
247 parameters | Absolute structure parameter: −0.05 (6) |
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 | 0.63940 (7) | 0.8435 (4) | 0.11796 (18) | 0.0177 (4) | |
C2 | 0.67868 (8) | 1.0065 (4) | 0.0840 (2) | 0.0219 (5) | |
H2 | 0.6760 (7) | 1.124 (5) | 0.013 (2) | 0.026* | |
C3 | 0.71927 (8) | 1.0039 (5) | 0.1583 (2) | 0.0242 (5) | |
H3 | 0.7474 (9) | 1.113 (4) | 0.134 (2) | 0.029* | |
C4 | 0.72028 (7) | 0.8437 (4) | 0.2661 (2) | 0.0194 (4) | |
H4 | 0.7483 (9) | 0.842 (4) | 0.315 (2) | 0.023* | |
C5 | 0.67987 (7) | 0.6855 (4) | 0.29759 (19) | 0.0146 (4) | |
C6 | 0.63895 (8) | 0.6804 (4) | 0.22407 (19) | 0.0175 (4) | |
H6 | 0.6131 (8) | 0.564 (4) | 0.250 (2) | 0.021* | |
C7 | 0.61813 (7) | 0.6853 (4) | 0.58859 (19) | 0.0154 (4) | |
C8 | 0.58006 (8) | 0.8235 (4) | 0.5321 (2) | 0.0179 (4) | |
H8 | 0.5841 (7) | 0.913 (4) | 0.469 (2) | 0.021* | |
C9 | 0.53528 (8) | 0.8283 (4) | 0.5895 (2) | 0.0188 (5) | |
H9 | 0.5118 (8) | 0.909 (4) | 0.551 (2) | 0.023* | |
C10 | 0.52982 (7) | 0.6906 (4) | 0.70080 (19) | 0.0166 (4) | |
C11 | 0.56676 (7) | 0.5508 (4) | 0.7602 (2) | 0.0181 (4) | |
H11 | 0.5631 (8) | 0.453 (4) | 0.831 (2) | 0.022* | |
C12 | 0.61079 (7) | 0.5526 (4) | 0.70134 (18) | 0.0155 (4) | |
S1 | 0.680852 (17) | 0.47848 (9) | 0.43241 (5) | 0.01655 (11) | |
N1 | 0.59615 (6) | 0.8425 (4) | 0.03865 (17) | 0.0234 (4) | |
N2 | 0.65165 (6) | 0.4156 (4) | 0.76543 (17) | 0.0200 (4) | |
N3 | 0.48240 (6) | 0.6976 (4) | 0.76390 (18) | 0.0238 (4) | |
O1 | 0.59276 (5) | 1.0242 (3) | −0.04173 (15) | 0.0303 (4) | |
O2 | 0.56581 (5) | 0.6588 (4) | 0.05693 (15) | 0.0279 (4) | |
O3 | 0.72932 (5) | 0.4132 (3) | 0.46165 (14) | 0.0247 (4) | |
O4 | 0.64466 (5) | 0.2683 (3) | 0.42225 (15) | 0.0211 (3) | |
O5 | 0.66457 (5) | 0.6961 (3) | 0.54078 (13) | 0.0179 (3) | |
O6 | 0.67106 (6) | 0.2177 (3) | 0.71487 (15) | 0.0339 (4) | |
O7 | 0.66216 (6) | 0.5114 (3) | 0.86734 (14) | 0.0299 (4) | |
O8 | 0.45300 (5) | 0.8714 (3) | 0.72981 (15) | 0.0321 (4) | |
O9 | 0.47545 (6) | 0.5267 (4) | 0.84620 (17) | 0.0437 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0152 (11) | 0.0196 (11) | 0.0182 (11) | 0.0031 (9) | −0.0017 (8) | −0.0035 (8) |
C2 | 0.0258 (12) | 0.0228 (11) | 0.0170 (11) | 0.0027 (10) | 0.0024 (9) | 0.0049 (9) |
C3 | 0.0216 (12) | 0.0256 (12) | 0.0255 (12) | −0.0049 (10) | 0.0046 (9) | 0.0056 (10) |
C4 | 0.0159 (11) | 0.0235 (11) | 0.0189 (11) | −0.0006 (9) | 0.0020 (9) | 0.0021 (10) |
C5 | 0.0151 (10) | 0.0144 (10) | 0.0142 (10) | 0.0048 (9) | 0.0024 (8) | 0.0031 (8) |
C6 | 0.0178 (10) | 0.0152 (10) | 0.0194 (12) | 0.0017 (9) | 0.0024 (9) | −0.0006 (8) |
C7 | 0.0152 (10) | 0.0149 (10) | 0.0160 (11) | −0.0028 (8) | 0.0035 (8) | −0.0025 (8) |
C8 | 0.0221 (11) | 0.0182 (11) | 0.0133 (11) | −0.0030 (9) | −0.0007 (9) | 0.0055 (8) |
C9 | 0.0163 (11) | 0.0203 (11) | 0.0197 (11) | 0.0007 (9) | −0.0049 (8) | 0.0009 (9) |
C10 | 0.0125 (10) | 0.0209 (11) | 0.0164 (11) | −0.0009 (8) | −0.0004 (8) | −0.0015 (8) |
C11 | 0.0194 (11) | 0.0215 (11) | 0.0134 (11) | −0.0022 (9) | 0.0007 (9) | 0.0019 (9) |
C12 | 0.0146 (10) | 0.0169 (10) | 0.0150 (11) | 0.0014 (8) | −0.0021 (8) | −0.0007 (8) |
S1 | 0.0162 (2) | 0.0174 (2) | 0.0160 (2) | 0.0025 (2) | 0.0025 (2) | 0.0041 (2) |
N1 | 0.0247 (10) | 0.0262 (10) | 0.0194 (10) | 0.0058 (9) | −0.0012 (8) | −0.0043 (8) |
N2 | 0.0179 (9) | 0.0263 (9) | 0.0159 (9) | −0.0004 (8) | 0.0014 (8) | 0.0062 (8) |
N3 | 0.0162 (9) | 0.0344 (11) | 0.0207 (10) | −0.0018 (8) | 0.0008 (8) | 0.0011 (9) |
O1 | 0.0361 (9) | 0.0296 (8) | 0.0253 (10) | 0.0083 (7) | −0.0088 (7) | 0.0082 (7) |
O2 | 0.0244 (8) | 0.0335 (9) | 0.0259 (9) | −0.0030 (8) | −0.0049 (7) | −0.0019 (7) |
O3 | 0.0200 (8) | 0.0312 (8) | 0.0230 (9) | 0.0079 (6) | 0.0020 (6) | 0.0093 (6) |
O4 | 0.0256 (8) | 0.0152 (6) | 0.0227 (8) | −0.0018 (6) | 0.0045 (7) | 0.0025 (6) |
O5 | 0.0136 (7) | 0.0221 (8) | 0.0181 (8) | −0.0027 (6) | 0.0023 (6) | 0.0015 (6) |
O6 | 0.0330 (9) | 0.0402 (10) | 0.0286 (10) | 0.0214 (8) | −0.0008 (8) | −0.0027 (8) |
O7 | 0.0291 (8) | 0.0388 (9) | 0.0218 (9) | 0.0056 (7) | −0.0101 (7) | 0.0005 (7) |
O8 | 0.0187 (8) | 0.0411 (9) | 0.0364 (11) | 0.0112 (7) | 0.0041 (7) | 0.0068 (8) |
O9 | 0.0219 (9) | 0.0711 (13) | 0.0382 (12) | 0.0029 (9) | 0.0073 (8) | 0.0315 (10) |
Geometric parameters (Å, º) top
C1—C6 | 1.380 (3) | C9—C10 | 1.374 (3) |
C1—C2 | 1.385 (3) | C9—H9 | 0.86 (2) |
C1—N1 | 1.473 (3) | C10—C11 | 1.378 (3) |
C2—C3 | 1.382 (3) | C10—N3 | 1.481 (2) |
C2—H2 | 0.95 (2) | C11—C12 | 1.376 (3) |
C3—C4 | 1.388 (3) | C11—H11 | 0.90 (2) |
C3—H3 | 0.97 (2) | C12—N2 | 1.477 (2) |
C4—C5 | 1.390 (3) | S1—O3 | 1.4147 (15) |
C4—H4 | 0.94 (2) | S1—O4 | 1.4182 (13) |
C5—C6 | 1.384 (3) | S1—O5 | 1.6222 (15) |
C5—S1 | 1.753 (2) | N1—O1 | 1.225 (2) |
C6—H6 | 0.95 (2) | N1—O2 | 1.227 (2) |
C7—C8 | 1.383 (3) | N2—O6 | 1.211 (2) |
C7—C12 | 1.384 (3) | N2—O7 | 1.224 (2) |
C7—O5 | 1.388 (2) | N3—O8 | 1.216 (2) |
C8—C9 | 1.387 (3) | N3—O9 | 1.216 (2) |
C8—H8 | 0.81 (2) | | |
| | | |
C6—C1—C2 | 122.58 (19) | C8—C9—H9 | 117.8 (16) |
C6—C1—N1 | 118.16 (18) | C9—C10—C11 | 123.52 (18) |
C2—C1—N1 | 119.27 (18) | C9—C10—N3 | 119.23 (17) |
C3—C2—C1 | 118.8 (2) | C11—C10—N3 | 117.22 (18) |
C3—C2—H2 | 122.4 (13) | C12—C11—C10 | 116.26 (19) |
C1—C2—H2 | 118.6 (13) | C12—C11—H11 | 119.6 (15) |
C2—C3—C4 | 120.5 (2) | C10—C11—H11 | 124.0 (15) |
C2—C3—H3 | 119.5 (14) | C11—C12—C7 | 122.58 (18) |
C4—C3—H3 | 120.0 (14) | C11—C12—N2 | 117.53 (17) |
C3—C4—C5 | 118.9 (2) | C7—C12—N2 | 119.85 (17) |
C3—C4—H4 | 119.5 (14) | O3—S1—O4 | 122.42 (8) |
C5—C4—H4 | 121.6 (14) | O3—S1—O5 | 104.06 (8) |
C6—C5—C4 | 122.03 (19) | O4—S1—O5 | 107.75 (8) |
C6—C5—S1 | 118.52 (16) | O3—S1—C5 | 108.77 (9) |
C4—C5—S1 | 119.43 (16) | O4—S1—C5 | 108.53 (10) |
C1—C6—C5 | 117.21 (19) | O5—S1—C5 | 103.71 (8) |
C1—C6—H6 | 125.3 (14) | O1—N1—O2 | 124.03 (18) |
C5—C6—H6 | 117.5 (14) | O1—N1—C1 | 118.10 (18) |
C8—C7—C12 | 119.30 (18) | O2—N1—C1 | 117.88 (17) |
C8—C7—O5 | 121.82 (18) | O6—N2—O7 | 125.83 (17) |
C12—C7—O5 | 118.65 (18) | O6—N2—C12 | 118.07 (17) |
C7—C8—C9 | 119.66 (19) | O7—N2—C12 | 116.08 (17) |
C7—C8—H8 | 120.9 (15) | O8—N3—O9 | 124.40 (18) |
C9—C8—H8 | 119.2 (15) | O8—N3—C10 | 118.16 (17) |
C10—C9—C8 | 118.7 (2) | O9—N3—C10 | 117.44 (17) |
C10—C9—H9 | 123.4 (16) | C7—O5—S1 | 120.15 (12) |
| | | |
C6—C1—C2—C3 | 0.7 (3) | C6—C5—S1—O3 | 154.18 (15) |
N1—C1—C2—C3 | −179.36 (19) | C4—C5—S1—O3 | −24.31 (19) |
C1—C2—C3—C4 | −1.0 (3) | C6—C5—S1—O4 | 18.87 (18) |
C2—C3—C4—C5 | 0.3 (3) | C4—C5—S1—O4 | −159.63 (15) |
C3—C4—C5—C6 | 0.7 (3) | C6—C5—S1—O5 | −95.51 (16) |
C3—C4—C5—S1 | 179.18 (16) | C4—C5—S1—O5 | 86.00 (17) |
C2—C1—C6—C5 | 0.2 (3) | C6—C1—N1—O1 | 166.58 (18) |
N1—C1—C6—C5 | −179.69 (17) | C2—C1—N1—O1 | −13.3 (3) |
C4—C5—C6—C1 | −1.0 (3) | C6—C1—N1—O2 | −13.7 (3) |
S1—C5—C6—C1 | −179.42 (15) | C2—C1—N1—O2 | 166.39 (18) |
C12—C7—C8—C9 | 0.3 (3) | C11—C12—N2—O6 | 119.0 (2) |
O5—C7—C8—C9 | −174.04 (19) | C7—C12—N2—O6 | −63.4 (2) |
C7—C8—C9—C10 | −1.0 (3) | C11—C12—N2—O7 | −59.6 (2) |
C8—C9—C10—C11 | 1.1 (3) | C7—C12—N2—O7 | 118.1 (2) |
C8—C9—C10—N3 | 179.11 (18) | C9—C10—N3—O8 | −15.3 (3) |
C9—C10—C11—C12 | −0.5 (3) | C11—C10—N3—O8 | 162.79 (19) |
N3—C10—C11—C12 | −178.51 (17) | C9—C10—N3—O9 | 164.2 (2) |
C10—C11—C12—C7 | −0.3 (3) | C11—C10—N3—O9 | −17.7 (3) |
C10—C11—C12—N2 | 177.28 (17) | C8—C7—O5—S1 | −84.7 (2) |
C8—C7—C12—C11 | 0.3 (3) | C12—C7—O5—S1 | 100.94 (19) |
O5—C7—C12—C11 | 174.87 (18) | O3—S1—O5—C7 | −142.85 (14) |
C8—C7—C12—N2 | −177.16 (17) | O4—S1—O5—C7 | −11.52 (16) |
O5—C7—C12—N2 | −2.6 (3) | C5—S1—O5—C7 | 103.41 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.95 (2) | 2.43 (2) | 2.742 (3) | 99.0 (15) |
C4—H4···O3 | 0.94 (2) | 2.63 (2) | 2.944 (3) | 100.4 (15) |
C6—H6···O2 | 0.95 (2) | 2.50 (2) | 2.715 (3) | 92.7 (15) |
C6—H6···O4 | 0.95 (2) | 2.49 (2) | 2.898 (2) | 106.4 (16) |
C9—H9···O8 | 0.86 (2) | 2.53 (2) | 2.745 (3) | 94.9 (18) |
C11—H11···O9 | 0.90 (2) | 2.46 (2) | 2.699 (3) | 95.3 (16) |
C2—H2···O7i | 0.95 (2) | 2.45 (2) | 3.374 (3) | 166.2 (19) |
C3—H3···O3ii | 0.97 (2) | 2.43 (2) | 3.208 (3) | 137.0 (18) |
C3—H3···O6ii | 0.97 (2) | 2.47 (2) | 3.263 (3) | 138.2 (18) |
C4—H4···O7iii | 0.94 (2) | 2.99 (2) | 3.781 (3) | 142.9 (17) |
C6—H6···N3iv | 0.95 (2) | 2.93 (2) | 3.836 (3) | 161.2 (18) |
C6—H6···O8iv | 0.95 (2) | 2.77 (2) | 3.652 (3) | 155.7 (19) |
C6—H6···O9iv | 0.95 (2) | 2.70 (2) | 3.572 (3) | 153.6 (17) |
C8—H8···O4v | 0.81 (2) | 2.43 (2) | 3.008 (2) | 129.2 (19) |
C8—H8···O8vi | 0.81 (2) | 2.96 (2) | 3.681 (3) | 150.0 (18) |
C9—H9···O2vii | 0.86 (2) | 2.97 (2) | 3.726 (3) | 147 (2) |
C11—H11···O1viii | 0.90 (2) | 2.58 (2) | 3.362 (3) | 145.1 (18) |
C11—H11···O2ix | 0.90 (2) | 2.62 (2) | 3.240 (3) | 126.4 (17) |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+3/2, y+1, z−1/2; (iii) −x+3/2, y, z−1/2; (iv) −x+1, −y+1, z−1/2; (v) x, y+1, z; (vi) −x+1, −y+2, z−1/2; (vii) −x+1, −y+2, z+1/2; (viii) x, y−1, z+1; (ix) x, y, z+1. |
Experimental details
Crystal data |
Chemical formula | C12H7N3O9S |
Mr | 369.27 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 120 |
a, b, c (Å) | 27.730 (2), 4.7374 (3), 10.7800 (8) |
V (Å3) | 1416.16 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.28 × 0.25 × 0.11 |
|
Data collection |
Diffractometer | Bruker SMART CCD 6K area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8989, 2952, 2619 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.641 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.059, 0.97 |
No. of reflections | 2952 |
No. of parameters | 247 |
No. of restraints | 1 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.34, −0.33 |
Absolute structure | (Flack, 1983); 1310 Friedel pairs |
Absolute structure parameter | −0.05 (6) |
Selected geometric parameters (Å, º) topC1—N1 | 1.473 (3) | N1—O1 | 1.225 (2) |
C5—S1 | 1.753 (2) | N1—O2 | 1.227 (2) |
C10—N3 | 1.481 (2) | N2—O6 | 1.211 (2) |
C12—N2 | 1.477 (2) | N2—O7 | 1.224 (2) |
S1—O3 | 1.4147 (15) | N3—O8 | 1.216 (2) |
S1—O4 | 1.4182 (13) | N3—O9 | 1.216 (2) |
S1—O5 | 1.6222 (15) | | |
| | | |
O3—S1—O4 | 122.42 (8) | O2—N1—C1 | 117.88 (17) |
O3—S1—O5 | 104.06 (8) | O6—N2—O7 | 125.83 (17) |
O4—S1—O5 | 107.75 (8) | O6—N2—C12 | 118.07 (17) |
O3—S1—C5 | 108.77 (9) | O7—N2—C12 | 116.08 (17) |
O4—S1—C5 | 108.53 (10) | O8—N3—O9 | 124.40 (18) |
O5—S1—C5 | 103.71 (8) | O8—N3—C10 | 118.16 (17) |
O1—N1—O2 | 124.03 (18) | O9—N3—C10 | 117.44 (17) |
O1—N1—C1 | 118.10 (18) | C7—O5—S1 | 120.15 (12) |
| | | |
C5—S1—O5—C7 | 103.41 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.95 (2) | 2.43 (2) | 2.742 (3) | 99.0 (15) |
C4—H4···O3 | 0.94 (2) | 2.63 (2) | 2.944 (3) | 100.4 (15) |
C6—H6···O2 | 0.95 (2) | 2.50 (2) | 2.715 (3) | 92.7 (15) |
C6—H6···O4 | 0.95 (2) | 2.49 (2) | 2.898 (2) | 106.4 (16) |
C9—H9···O8 | 0.86 (2) | 2.53 (2) | 2.745 (3) | 94.9 (18) |
C11—H11···O9 | 0.90 (2) | 2.46 (2) | 2.699 (3) | 95.3 (16) |
C2—H2···O7i | 0.95 (2) | 2.45 (2) | 3.374 (3) | 166.2 (19) |
C3—H3···O3ii | 0.97 (2) | 2.43 (2) | 3.208 (3) | 137.0 (18) |
C3—H3···O6ii | 0.97 (2) | 2.47 (2) | 3.263 (3) | 138.2 (18) |
C4—H4···O7iii | 0.94 (2) | 2.99 (2) | 3.781 (3) | 142.9 (17) |
C6—H6···N3iv | 0.95 (2) | 2.93 (2) | 3.836 (3) | 161.2 (18) |
C6—H6···O8iv | 0.95 (2) | 2.77 (2) | 3.652 (3) | 155.7 (19) |
C6—H6···O9iv | 0.95 (2) | 2.70 (2) | 3.572 (3) | 153.6 (17) |
C8—H8···O4v | 0.81 (2) | 2.43 (2) | 3.008 (2) | 129.2 (19) |
C8—H8···O8vi | 0.81 (2) | 2.96 (2) | 3.681 (3) | 150.0 (18) |
C9—H9···O2vii | 0.86 (2) | 2.97 (2) | 3.726 (3) | 147 (2) |
C11—H11···O1viii | 0.90 (2) | 2.58 (2) | 3.362 (3) | 145.1 (18) |
C11—H11···O2ix | 0.90 (2) | 2.62 (2) | 3.240 (3) | 126.4 (17) |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+3/2, y+1, z−1/2; (iii) −x+3/2, y, z−1/2; (iv) −x+1, −y+1, z−1/2; (v) x, y+1, z; (vi) −x+1, −y+2, z−1/2; (vii) −x+1, −y+2, z+1/2; (viii) x, y−1, z+1; (ix) x, y, z+1. |
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 structures of 3-nitrobenzenesulfonyl chloride have been recently reported (Vembu Nallu Spencer & Howard, 2003c). An X-ray study of the title compound, (I), was undertaken in view of the biological importance of its analogues and also to compare its structural parameters with those of its precursor, 3-nitrobenzenesulfonyl chloride.
The molecular structure of (I) is 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 0.005 (3), −0.248 (4) and 0.267 (4) Å, respectively. Atoms N2, O6, O7, N3, O8 and O9 deviate from the mean plane formed by atoms C7—C12 by 0.069 (3), −0.849 (3), 1.051 (3), 0.026 (3), 0.341 (4) and −0.277 (4) Å, respectively. The dihedral angle between the above-mentioned planes is 36.10 (7)°. This shows their non-coplanar orientation, similar to that reported for some aromatic sulfonates (Vembu Nallu Garrison & Youngs, 2003b-e; Vembu Nallu Spencer & Howard, 2003a,b,d,e), and in contrast with the near-coplanar orientation found in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu Nallu Garrison & Youngs, 2003a) and 4-methoxyphenyl 4-toluenesulfonate (Vembu et al., 2003).
The crystal structure of (I) 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 C2—H2···O1, C4—H4···O3, C6—H6···O2, C6—H6···O4, C9—H9···O8 and C11—H11···O9 interaction generates an 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 can be seen in Fig. 3, the C3—H3···O3ii and C3—H3···O6ii interactions constitute a pair of bifurcated donor bonds generating an R12(8) motif. The C6—H6···N3iv, C6—H6···O8iv and C6—H6···O9iv interactions together constitute a set of trifurcated donor bonds. The C6—H6···O8iv and C6—H6···O9iv interactions generate a symmetrical three-centred hydrogen-bonded chelate motif of graph set R12(4). There are several other weak C—H···O interactions which contribute to the supramolecular aggregation of (I) (Table 2). Other short intermolecular contacts are C9···O9(1 − x, 1 − y, z − 1/2) 3.130 (3) Å, N1···O8(1 − x, 2 − y, z − 1/2) 2.818 (2) Å and N1···O7(x, y, z − 1) 3.037 (2) Å. A view of the molecular packing down the b axis is shown in Fig. 4.