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In the title mol­ecule, C12H9NO5S, there are weak C—H...O interactions which generate rings of motifs S(5), S(6), R21(4), R12(5), R22(7) and R22(13). The supramolecular aggregation is completed by the presence of C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015964/ob6276sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015964/ob6276Isup2.hkl
Contains datablock I

CCDC reference: 221714

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.060
  • Data-to-parameter ratio = 12.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.51 From the CIF: _reflns_number_total 2392 Count of symmetry unique reflns 1495 Completeness (_total/calc) 160.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 897 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes 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.

Computing details top

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.

Phenyl 3-nitrobenzenesulfonate top
Crystal data top
C12H9NO5SDx = 1.575 Mg m3
Mr = 279.26Melting point = 363–365 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 713 reflections
a = 17.458 (4) Åθ = 2.9–25.7°
b = 12.287 (3) ŵ = 0.29 mm1
c = 5.4891 (14) ÅT = 120 K
V = 1177.4 (5) Å3Block, colourless
Z = 40.16 × 0.14 × 0.09 mm
F(000) = 576
Data collection top
Bruker Proteum M
diffractometer
1838 reflections with I > 2σ(I)
Radiation source: Bede microsourceRint = 0.059
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
Detector resolution: 8 pixels mm-1h = 2222
/w scansk = 1512
7868 measured reflectionsl = 75
2392 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Only H-atom coordinates refined
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0153P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
2392 reflectionsΔρmax = 0.44 e Å3
199 parametersΔρmin = 0.47 e Å3
1 restraintAbsolute structure: (Flack, 1983), 897 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (8)
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
xyzUiso*/Ueq
C10.11247 (15)0.0630 (2)0.7016 (6)0.0182 (6)
C20.11324 (17)0.1622 (2)0.5871 (5)0.0199 (7)
H20.0838 (16)0.217 (2)0.639 (5)0.024*
C30.15896 (17)0.1769 (2)0.3843 (5)0.0217 (8)
H30.1607 (14)0.2488 (19)0.299 (5)0.026*
C40.20411 (15)0.0918 (2)0.3034 (6)0.0184 (6)
H40.2345 (14)0.099 (2)0.171 (5)0.022*
C50.20319 (15)0.0061 (2)0.4260 (5)0.0160 (6)
C60.15734 (16)0.0239 (2)0.6291 (5)0.0159 (6)
H60.1562 (13)0.089 (2)0.724 (5)0.019*
C70.37909 (15)0.0097 (2)0.4286 (6)0.0176 (6)
C80.36942 (16)0.0896 (2)0.6005 (6)0.0212 (7)
H80.3416 (15)0.074 (2)0.734 (5)0.025*
C90.40583 (17)0.1882 (2)0.5661 (6)0.0231 (7)
H90.4006 (15)0.2436 (19)0.681 (6)0.028*
C100.44987 (16)0.2057 (2)0.3633 (6)0.0220 (7)
H100.4720 (14)0.276 (2)0.336 (6)0.026*
C110.45943 (16)0.1234 (2)0.1933 (6)0.0234 (7)
H110.4901 (15)0.136 (2)0.061 (5)0.028*
C120.42409 (16)0.0234 (2)0.2258 (6)0.0206 (7)
H120.4291 (14)0.031 (2)0.112 (5)0.025*
N10.06214 (13)0.0485 (2)0.9160 (4)0.0238 (6)
O10.02181 (11)0.12588 (16)0.9769 (4)0.0314 (6)
O20.06358 (11)0.03936 (16)1.0221 (4)0.0287 (5)
O30.23727 (11)0.21412 (14)0.4141 (3)0.0249 (5)
O40.27614 (11)0.09700 (14)0.0710 (3)0.0251 (5)
O50.34119 (11)0.09175 (14)0.4680 (3)0.0198 (5)
S10.26294 (4)0.11242 (5)0.32360 (13)0.01894 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0139 (15)0.0243 (16)0.0163 (15)0.0034 (11)0.0031 (14)0.0026 (14)
C20.0197 (17)0.0186 (16)0.0214 (18)0.0025 (13)0.0037 (15)0.0052 (14)
C30.0210 (16)0.0164 (15)0.028 (2)0.0033 (12)0.0079 (14)0.0023 (13)
C40.0167 (14)0.0229 (15)0.0155 (14)0.0031 (11)0.0021 (14)0.0011 (15)
C50.0131 (14)0.0168 (14)0.0180 (16)0.0011 (11)0.0039 (13)0.0034 (12)
C60.0167 (15)0.0162 (14)0.0148 (16)0.0020 (12)0.0051 (12)0.0020 (12)
C70.0149 (14)0.0172 (14)0.0208 (17)0.0029 (12)0.0011 (14)0.0039 (13)
C80.0191 (16)0.0296 (17)0.0147 (16)0.0006 (13)0.0003 (14)0.0036 (14)
C90.0193 (17)0.0271 (18)0.023 (2)0.0014 (13)0.0037 (15)0.0044 (14)
C100.0173 (15)0.0222 (15)0.026 (2)0.0026 (12)0.0031 (14)0.0054 (14)
C110.0210 (17)0.0300 (18)0.0193 (16)0.0029 (13)0.0053 (15)0.0020 (16)
C120.0193 (16)0.0213 (16)0.0211 (18)0.0060 (12)0.0002 (15)0.0014 (13)
N10.0198 (14)0.0341 (15)0.0174 (14)0.0037 (12)0.0021 (12)0.0067 (12)
O10.0266 (13)0.0356 (13)0.0321 (14)0.0070 (10)0.0039 (11)0.0120 (11)
O20.0294 (13)0.0319 (12)0.0249 (12)0.0061 (10)0.0051 (11)0.0028 (10)
O30.0254 (11)0.0193 (10)0.0301 (13)0.0028 (9)0.0015 (11)0.0031 (8)
O40.0297 (12)0.0261 (11)0.0195 (11)0.0043 (9)0.0003 (10)0.0042 (10)
O50.0174 (10)0.0206 (10)0.0214 (11)0.0012 (8)0.0017 (9)0.0049 (8)
S10.0206 (3)0.0175 (3)0.0187 (3)0.0016 (3)0.0006 (4)0.0016 (4)
Geometric parameters (Å, º) top
C1—C21.371 (4)C8—C91.382 (4)
C1—C61.382 (4)C8—H80.90 (3)
C1—N11.480 (4)C9—C101.370 (4)
C2—C31.382 (4)C9—H90.93 (3)
C2—H20.89 (3)C10—C111.386 (4)
C3—C41.382 (4)C10—H100.95 (2)
C3—H31.00 (2)C11—C121.387 (4)
C4—C51.379 (4)C11—H110.91 (3)
C4—H40.90 (3)C12—H120.92 (3)
C5—C61.390 (4)N1—O21.226 (3)
C5—S11.763 (3)N1—O11.230 (3)
C6—H60.96 (3)O3—S11.4175 (18)
C7—C81.372 (4)O4—S11.418 (2)
C7—C121.373 (4)O5—S11.600 (2)
C7—O51.427 (3)
C2—C1—C6123.3 (3)C9—C8—H8123.0 (17)
C2—C1—N1118.5 (3)C10—C9—C8120.5 (3)
C6—C1—N1118.2 (2)C10—C9—H9119.4 (17)
C1—C2—C3119.4 (3)C8—C9—H9120.1 (17)
C1—C2—H2121.1 (18)C9—C10—C11120.0 (3)
C3—C2—H2119.5 (18)C9—C10—H10119.9 (18)
C2—C3—C4119.3 (3)C11—C10—H10120.1 (18)
C2—C3—H3120.7 (15)C12—C11—C10120.4 (3)
C4—C3—H3120.0 (15)C12—C11—H11120.6 (17)
C5—C4—C3119.8 (3)C10—C11—H11119.0 (17)
C5—C4—H4118.7 (17)C7—C12—C11117.9 (3)
C3—C4—H4121.6 (17)C7—C12—H12121.2 (17)
C4—C5—C6122.4 (3)C11—C12—H12120.8 (17)
C4—C5—S1118.9 (2)O2—N1—O1124.3 (3)
C6—C5—S1118.7 (2)O2—N1—C1118.1 (2)
C1—C6—C5115.9 (3)O1—N1—C1117.6 (2)
C1—C6—H6118.7 (15)C7—O5—S1117.36 (16)
C5—C6—H6125.4 (16)O3—S1—O4120.78 (11)
C8—C7—C12122.7 (3)O3—S1—O5103.67 (10)
C8—C7—O5117.6 (3)O4—S1—O5108.94 (11)
C12—C7—O5119.7 (3)O3—S1—C5110.74 (13)
C7—C8—C9118.5 (3)O4—S1—C5107.98 (13)
C7—C8—H8118.4 (17)O5—S1—C5103.28 (11)
C6—C1—C2—C32.1 (4)C10—C11—C12—C70.8 (4)
N1—C1—C2—C3179.0 (2)C2—C1—N1—O2177.7 (3)
C1—C2—C3—C41.2 (4)C6—C1—N1—O21.3 (4)
C2—C3—C4—C50.2 (4)C2—C1—N1—O11.9 (4)
C3—C4—C5—C60.8 (4)C6—C1—N1—O1179.1 (2)
C3—C4—C5—S1178.5 (2)C8—C7—O5—S1100.0 (3)
C2—C1—C6—C51.4 (4)C12—C7—O5—S180.9 (3)
N1—C1—C6—C5179.6 (2)C7—O5—S1—O3175.80 (19)
C4—C5—C6—C10.0 (4)C7—O5—S1—O454.4 (2)
S1—C5—C6—C1179.3 (2)C7—O5—S1—C560.2 (2)
C12—C7—C8—C90.8 (4)C4—C5—S1—O3160.8 (2)
O5—C7—C8—C9179.8 (2)C6—C5—S1—O319.8 (2)
C7—C8—C9—C100.6 (5)C4—C5—S1—O426.5 (2)
C8—C9—C10—C111.3 (5)C6—C5—S1—O4154.1 (2)
C9—C10—C11—C120.5 (4)C4—C5—S1—O588.8 (2)
C8—C7—C12—C111.5 (4)C6—C5—S1—O590.6 (2)
O5—C7—C12—C11179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.89 (2)2.42 (3)2.707 (4)98.8 (18)
C4—H4···O40.90 (2)2.57 (2)2.932 (3)104.5 (17)
C6—H6···O20.94 (2)2.39 (2)2.715 (4)100.2 (15)
C6—H6···O30.94 (2)2.69 (2)2.968 (3)97.7 (16)
C12—H12···O40.90 (3)2.80 (2)3.095 (3)100.4 (18)
C3—H3···O3i1.00 (2)2.80 (3)3.426 (4)121.2 (17)
C3—H3···O5i1.00 (2)2.67 (3)3.647 (3)165 (2)
C9—H9···O2i0.93 (3)2.87 (2)3.399 (4)117 (2)
C10—H10···O2i0.94 (2)2.58 (2)3.260 (3)129.6 (19)
C4—H4···O3i0.90 (2)2.75 (2)3.364 (4)127.0 (18)
C9—H9···O3ii0.93 (3)2.78 (3)3.366 (4)121.7 (19)
C3—H3···O4ii1.00 (2)2.65 (2)3.170 (3)112.2 (19)
C6—H6···O4iii0.94 (2)2.84 (2)3.317 (3)112.9 (15)
C10—H10···O1iv0.94 (2)2.48 (3)3.219 (4)135 (2)
C4—H4···Cg20.90 (2)3.383.72105
C12—H12···Cg2v0.90 (3)3.133.71124
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x+1/2, y+1/2, z1; (v) x+1, y, z1/2.
 

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