In the title molecule, C
12H
9NO
5S, 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
CCDC reference: 221714
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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.
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
C12H9NO5S | Dx = 1.575 Mg m−3 |
Mr = 279.26 | Melting point = 363–365 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 713 reflections |
a = 17.458 (4) Å | θ = 2.9–25.7° |
b = 12.287 (3) Å | µ = 0.29 mm−1 |
c = 5.4891 (14) Å | T = 120 K |
V = 1177.4 (5) Å3 | Block, colourless |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
F(000) = 576 | |
Data collection top
Bruker Proteum M diffractometer | 1838 reflections with I > 2σ(I) |
Radiation source: Bede microsource | Rint = 0.059 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
Detector resolution: 8 pixels mm-1 | h = −22→22 |
/w scans | k = −15→12 |
7868 measured reflections | l = −7→5 |
2392 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Only 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 reflections | Δρmax = 0.44 e Å−3 |
199 parameters | Δρmin = −0.47 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983), 897 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.11247 (15) | 0.0630 (2) | 0.7016 (6) | 0.0182 (6) | |
C2 | 0.11324 (17) | 0.1622 (2) | 0.5871 (5) | 0.0199 (7) | |
H2 | 0.0838 (16) | 0.217 (2) | 0.639 (5) | 0.024* | |
C3 | 0.15896 (17) | 0.1769 (2) | 0.3843 (5) | 0.0217 (8) | |
H3 | 0.1607 (14) | 0.2488 (19) | 0.299 (5) | 0.026* | |
C4 | 0.20411 (15) | 0.0918 (2) | 0.3034 (6) | 0.0184 (6) | |
H4 | 0.2345 (14) | 0.099 (2) | 0.171 (5) | 0.022* | |
C5 | 0.20319 (15) | −0.0061 (2) | 0.4260 (5) | 0.0160 (6) | |
C6 | 0.15734 (16) | −0.0239 (2) | 0.6291 (5) | 0.0159 (6) | |
H6 | 0.1562 (13) | −0.089 (2) | 0.724 (5) | 0.019* | |
C7 | 0.37909 (15) | 0.0097 (2) | 0.4286 (6) | 0.0176 (6) | |
C8 | 0.36942 (16) | 0.0896 (2) | 0.6005 (6) | 0.0212 (7) | |
H8 | 0.3416 (15) | 0.074 (2) | 0.734 (5) | 0.025* | |
C9 | 0.40583 (17) | 0.1882 (2) | 0.5661 (6) | 0.0231 (7) | |
H9 | 0.4006 (15) | 0.2436 (19) | 0.681 (6) | 0.028* | |
C10 | 0.44987 (16) | 0.2057 (2) | 0.3633 (6) | 0.0220 (7) | |
H10 | 0.4720 (14) | 0.276 (2) | 0.336 (6) | 0.026* | |
C11 | 0.45943 (16) | 0.1234 (2) | 0.1933 (6) | 0.0234 (7) | |
H11 | 0.4901 (15) | 0.136 (2) | 0.061 (5) | 0.028* | |
C12 | 0.42409 (16) | 0.0234 (2) | 0.2258 (6) | 0.0206 (7) | |
H12 | 0.4291 (14) | −0.031 (2) | 0.112 (5) | 0.025* | |
N1 | 0.06214 (13) | 0.0485 (2) | 0.9160 (4) | 0.0238 (6) | |
O1 | 0.02181 (11) | 0.12588 (16) | 0.9769 (4) | 0.0314 (6) | |
O2 | 0.06358 (11) | −0.03936 (16) | 1.0221 (4) | 0.0287 (5) | |
O3 | 0.23727 (11) | −0.21412 (14) | 0.4141 (3) | 0.0249 (5) | |
O4 | 0.27614 (11) | −0.09700 (14) | 0.0710 (3) | 0.0251 (5) | |
O5 | 0.34119 (11) | −0.09175 (14) | 0.4680 (3) | 0.0198 (5) | |
S1 | 0.26294 (4) | −0.11242 (5) | 0.32360 (13) | 0.01894 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0139 (15) | 0.0243 (16) | 0.0163 (15) | −0.0034 (11) | −0.0031 (14) | −0.0026 (14) |
C2 | 0.0197 (17) | 0.0186 (16) | 0.0214 (18) | 0.0025 (13) | −0.0037 (15) | −0.0052 (14) |
C3 | 0.0210 (16) | 0.0164 (15) | 0.028 (2) | −0.0033 (12) | −0.0079 (14) | 0.0023 (13) |
C4 | 0.0167 (14) | 0.0229 (15) | 0.0155 (14) | −0.0031 (11) | −0.0021 (14) | −0.0011 (15) |
C5 | 0.0131 (14) | 0.0168 (14) | 0.0180 (16) | 0.0011 (11) | −0.0039 (13) | −0.0034 (12) |
C6 | 0.0167 (15) | 0.0162 (14) | 0.0148 (16) | −0.0020 (12) | −0.0051 (12) | −0.0020 (12) |
C7 | 0.0149 (14) | 0.0172 (14) | 0.0208 (17) | 0.0029 (12) | −0.0011 (14) | 0.0039 (13) |
C8 | 0.0191 (16) | 0.0296 (17) | 0.0147 (16) | −0.0006 (13) | 0.0003 (14) | 0.0036 (14) |
C9 | 0.0193 (17) | 0.0271 (18) | 0.023 (2) | 0.0014 (13) | −0.0037 (15) | −0.0044 (14) |
C10 | 0.0173 (15) | 0.0222 (15) | 0.026 (2) | −0.0026 (12) | −0.0031 (14) | 0.0054 (14) |
C11 | 0.0210 (17) | 0.0300 (18) | 0.0193 (16) | 0.0029 (13) | 0.0053 (15) | 0.0020 (16) |
C12 | 0.0193 (16) | 0.0213 (16) | 0.0211 (18) | 0.0060 (12) | 0.0002 (15) | −0.0014 (13) |
N1 | 0.0198 (14) | 0.0341 (15) | 0.0174 (14) | −0.0037 (12) | −0.0021 (12) | −0.0067 (12) |
O1 | 0.0266 (13) | 0.0356 (13) | 0.0321 (14) | 0.0070 (10) | 0.0039 (11) | −0.0120 (11) |
O2 | 0.0294 (13) | 0.0319 (12) | 0.0249 (12) | −0.0061 (10) | 0.0051 (11) | 0.0028 (10) |
O3 | 0.0254 (11) | 0.0193 (10) | 0.0301 (13) | −0.0028 (9) | −0.0015 (11) | −0.0031 (8) |
O4 | 0.0297 (12) | 0.0261 (11) | 0.0195 (11) | 0.0043 (9) | −0.0003 (10) | −0.0042 (10) |
O5 | 0.0174 (10) | 0.0206 (10) | 0.0214 (11) | 0.0012 (8) | −0.0017 (9) | 0.0049 (8) |
S1 | 0.0206 (3) | 0.0175 (3) | 0.0187 (3) | 0.0016 (3) | 0.0006 (4) | −0.0016 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.371 (4) | C8—C9 | 1.382 (4) |
C1—C6 | 1.382 (4) | C8—H8 | 0.90 (3) |
C1—N1 | 1.480 (4) | C9—C10 | 1.370 (4) |
C2—C3 | 1.382 (4) | C9—H9 | 0.93 (3) |
C2—H2 | 0.89 (3) | C10—C11 | 1.386 (4) |
C3—C4 | 1.382 (4) | C10—H10 | 0.95 (2) |
C3—H3 | 1.00 (2) | C11—C12 | 1.387 (4) |
C4—C5 | 1.379 (4) | C11—H11 | 0.91 (3) |
C4—H4 | 0.90 (3) | C12—H12 | 0.92 (3) |
C5—C6 | 1.390 (4) | N1—O2 | 1.226 (3) |
C5—S1 | 1.763 (3) | N1—O1 | 1.230 (3) |
C6—H6 | 0.96 (3) | O3—S1 | 1.4175 (18) |
C7—C8 | 1.372 (4) | O4—S1 | 1.418 (2) |
C7—C12 | 1.373 (4) | O5—S1 | 1.600 (2) |
C7—O5 | 1.427 (3) | | |
| | | |
C2—C1—C6 | 123.3 (3) | C9—C8—H8 | 123.0 (17) |
C2—C1—N1 | 118.5 (3) | C10—C9—C8 | 120.5 (3) |
C6—C1—N1 | 118.2 (2) | C10—C9—H9 | 119.4 (17) |
C1—C2—C3 | 119.4 (3) | C8—C9—H9 | 120.1 (17) |
C1—C2—H2 | 121.1 (18) | C9—C10—C11 | 120.0 (3) |
C3—C2—H2 | 119.5 (18) | C9—C10—H10 | 119.9 (18) |
C2—C3—C4 | 119.3 (3) | C11—C10—H10 | 120.1 (18) |
C2—C3—H3 | 120.7 (15) | C12—C11—C10 | 120.4 (3) |
C4—C3—H3 | 120.0 (15) | C12—C11—H11 | 120.6 (17) |
C5—C4—C3 | 119.8 (3) | C10—C11—H11 | 119.0 (17) |
C5—C4—H4 | 118.7 (17) | C7—C12—C11 | 117.9 (3) |
C3—C4—H4 | 121.6 (17) | C7—C12—H12 | 121.2 (17) |
C4—C5—C6 | 122.4 (3) | C11—C12—H12 | 120.8 (17) |
C4—C5—S1 | 118.9 (2) | O2—N1—O1 | 124.3 (3) |
C6—C5—S1 | 118.7 (2) | O2—N1—C1 | 118.1 (2) |
C1—C6—C5 | 115.9 (3) | O1—N1—C1 | 117.6 (2) |
C1—C6—H6 | 118.7 (15) | C7—O5—S1 | 117.36 (16) |
C5—C6—H6 | 125.4 (16) | O3—S1—O4 | 120.78 (11) |
C8—C7—C12 | 122.7 (3) | O3—S1—O5 | 103.67 (10) |
C8—C7—O5 | 117.6 (3) | O4—S1—O5 | 108.94 (11) |
C12—C7—O5 | 119.7 (3) | O3—S1—C5 | 110.74 (13) |
C7—C8—C9 | 118.5 (3) | O4—S1—C5 | 107.98 (13) |
C7—C8—H8 | 118.4 (17) | O5—S1—C5 | 103.28 (11) |
| | | |
C6—C1—C2—C3 | 2.1 (4) | C10—C11—C12—C7 | 0.8 (4) |
N1—C1—C2—C3 | −179.0 (2) | C2—C1—N1—O2 | −177.7 (3) |
C1—C2—C3—C4 | −1.2 (4) | C6—C1—N1—O2 | 1.3 (4) |
C2—C3—C4—C5 | −0.2 (4) | C2—C1—N1—O1 | 1.9 (4) |
C3—C4—C5—C6 | 0.8 (4) | C6—C1—N1—O1 | −179.1 (2) |
C3—C4—C5—S1 | −178.5 (2) | C8—C7—O5—S1 | 100.0 (3) |
C2—C1—C6—C5 | −1.4 (4) | C12—C7—O5—S1 | −80.9 (3) |
N1—C1—C6—C5 | 179.6 (2) | C7—O5—S1—O3 | −175.80 (19) |
C4—C5—C6—C1 | 0.0 (4) | C7—O5—S1—O4 | 54.4 (2) |
S1—C5—C6—C1 | 179.3 (2) | C7—O5—S1—C5 | −60.2 (2) |
C12—C7—C8—C9 | 0.8 (4) | C4—C5—S1—O3 | −160.8 (2) |
O5—C7—C8—C9 | 179.8 (2) | C6—C5—S1—O3 | 19.8 (2) |
C7—C8—C9—C10 | 0.6 (5) | C4—C5—S1—O4 | −26.5 (2) |
C8—C9—C10—C11 | −1.3 (5) | C6—C5—S1—O4 | 154.1 (2) |
C9—C10—C11—C12 | 0.5 (4) | C4—C5—S1—O5 | 88.8 (2) |
C8—C7—C12—C11 | −1.5 (4) | C6—C5—S1—O5 | −90.6 (2) |
O5—C7—C12—C11 | 179.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.89 (2) | 2.42 (3) | 2.707 (4) | 98.8 (18) |
C4—H4···O4 | 0.90 (2) | 2.57 (2) | 2.932 (3) | 104.5 (17) |
C6—H6···O2 | 0.94 (2) | 2.39 (2) | 2.715 (4) | 100.2 (15) |
C6—H6···O3 | 0.94 (2) | 2.69 (2) | 2.968 (3) | 97.7 (16) |
C12—H12···O4 | 0.90 (3) | 2.80 (2) | 3.095 (3) | 100.4 (18) |
C3—H3···O3i | 1.00 (2) | 2.80 (3) | 3.426 (4) | 121.2 (17) |
C3—H3···O5i | 1.00 (2) | 2.67 (3) | 3.647 (3) | 165 (2) |
C9—H9···O2i | 0.93 (3) | 2.87 (2) | 3.399 (4) | 117 (2) |
C10—H10···O2i | 0.94 (2) | 2.58 (2) | 3.260 (3) | 129.6 (19) |
C4—H4···O3i | 0.90 (2) | 2.75 (2) | 3.364 (4) | 127.0 (18) |
C9—H9···O3ii | 0.93 (3) | 2.78 (3) | 3.366 (4) | 121.7 (19) |
C3—H3···O4ii | 1.00 (2) | 2.65 (2) | 3.170 (3) | 112.2 (19) |
C6—H6···O4iii | 0.94 (2) | 2.84 (2) | 3.317 (3) | 112.9 (15) |
C10—H10···O1iv | 0.94 (2) | 2.48 (3) | 3.219 (4) | 135 (2) |
C4—H4···Cg2 | 0.90 (2) | 3.38 | 3.72 | 105 |
C12—H12···Cg2v | 0.90 (3) | 3.13 | 3.71 | 124 |
Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) −x+1/2, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x+1/2, −y+1/2, z−1; (v) −x+1, −y, z−1/2. |