In the crystal structure of the title compound, C
13H
11NO
5S, the dihedral angle between the mean planes of the 4-tolyl and 4-nitrophenyl rings is 82.52 (4)°. There are weak C—H
O interactions, which generate rings of graph-set motifs
S(5),
S(6),
(5),
(6) and
(9). The supramolecular aggregation is completed by the presence of C—H
π and van der Waals interactions.
Supporting information
CCDC reference: 262451
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 35.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: The slightly low completeness at theta max = 37 deg is a
result of collecting data to such an exceptionally high scattering
angle,but it does not present a problem, since the data/parameter ratio is
also extremely high, at theta>30
|
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H7B .. O2 .. 3.00 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O2 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O3 .. 2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O2 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O1 .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O4 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O5 .. 2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CG .. 3.07 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. O2 .. 3.89 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C6 .. O2 .. 92.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C6 .. O3 .. 95.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C10 .. O5 .. 98.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C12 .. O4 .. 98.00 Deg.
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
14 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
2 ALERT type 3 Indicator that the structure quality may be low
14 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
4-Nitrophenyl 4-toluenesulfonate
top
Crystal data top
C13H11NO5S | F(000) = 608 |
Mr = 293.29 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/c | Melting point = 368–369 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3450 (4) Å | Cell parameters from 7340 reflections |
b = 8.0160 (4) Å | θ = 2.5–37.0° |
c = 12.3780 (7) Å | µ = 0.27 mm−1 |
β = 104.391 (3)° | T = 150 K |
V = 1282.57 (10) Å3 | Prism, colorless |
Z = 4 | 0.37 × 0.27 × 0.10 mm |
Data collection top
Nonius KappaCCD (with Oxford Cryosystems Cryostream cooler) diffractometer | 6437 independent reflections |
Radiation source: fine-focus sealed tube | 3045 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans with κ offsets | θmax = 37.1°, θmin = 2.8° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −22→22 |
Tmin = 0.887, Tmax = 0.973 | k = −13→13 |
10707 measured reflections | l = −19→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3 |
6437 reflections | (Δ/σ)max = 0.001 |
184 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.52 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 | 0.75945 (2) | 0.17905 (4) | 0.23933 (2) | 0.02194 (7) | |
O1 | 0.77600 (6) | 0.05565 (10) | 0.32526 (6) | 0.02801 (19) | |
O2 | 0.73660 (6) | 0.34616 (10) | 0.26385 (6) | 0.02787 (19) | |
O3 | 0.66279 (6) | 0.12985 (10) | 0.14016 (6) | 0.02253 (17) | |
O4 | 0.59890 (7) | −0.60198 (10) | −0.04324 (7) | 0.0333 (2) | |
O5 | 0.53415 (7) | −0.46018 (11) | −0.19332 (6) | 0.0352 (2) | |
N1 | 0.57873 (7) | −0.46928 (12) | −0.09395 (7) | 0.0241 (2) | |
C1 | 0.86393 (8) | 0.17603 (13) | 0.17674 (8) | 0.0204 (2) | |
C2 | 0.95129 (9) | 0.08355 (15) | 0.22504 (9) | 0.0270 (3) | |
H2 | 0.9532 | 0.0177 | 0.2874 | 0.0346 (13)* | |
C3 | 1.03629 (9) | 0.09078 (15) | 0.17870 (9) | 0.0315 (3) | |
H3 | 1.0957 | 0.0307 | 0.2114 | 0.0346 (13)* | |
C4 | 1.03351 (9) | 0.18646 (15) | 0.08428 (9) | 0.0265 (2) | |
C5 | 0.94383 (9) | 0.27559 (16) | 0.03685 (9) | 0.0282 (3) | |
H5 | 0.9409 | 0.3389 | −0.0268 | 0.0346 (13)* | |
C6 | 0.85901 (9) | 0.27227 (15) | 0.08211 (9) | 0.0257 (2) | |
H6 | 0.7998 | 0.3332 | 0.0499 | 0.0346 (13)* | |
C7 | 1.12573 (10) | 0.19353 (18) | 0.03422 (11) | 0.0389 (3) | |
H7A | 1.1033 | 0.1756 | −0.0448 | 0.096 (4)* | |
H7B | 1.1744 | 0.1085 | 0.0672 | 0.096 (4)* | |
H7C | 1.1581 | 0.3010 | 0.0485 | 0.096 (4)* | |
C8 | 0.65328 (8) | −0.02578 (13) | 0.08513 (8) | 0.0195 (2) | |
C9 | 0.61525 (9) | −0.01708 (14) | −0.02953 (8) | 0.0221 (2) | |
H9 | 0.6060 | 0.0855 | −0.0658 | 0.0346 (13)* | |
C10 | 0.59132 (8) | −0.16410 (13) | −0.08905 (8) | 0.0210 (2) | |
H10 | 0.5641 | −0.1623 | −0.1659 | 0.0346 (13)* | |
C11 | 0.60875 (8) | −0.31398 (13) | −0.03178 (8) | 0.0204 (2) | |
C12 | 0.64936 (9) | −0.32318 (14) | 0.08232 (8) | 0.0238 (2) | |
H12 | 0.6613 | −0.4260 | 0.1181 | 0.0346 (13)* | |
C13 | 0.67188 (9) | −0.17601 (14) | 0.14228 (8) | 0.0240 (2) | |
H13 | 0.6989 | −0.1780 | 0.2191 | 0.0346 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.02256 (13) | 0.02290 (14) | 0.02041 (12) | −0.00249 (12) | 0.00547 (10) | −0.00321 (11) |
O1 | 0.0315 (5) | 0.0316 (5) | 0.0201 (4) | −0.0053 (4) | 0.0048 (3) | 0.0027 (3) |
O2 | 0.0297 (4) | 0.0245 (4) | 0.0312 (4) | −0.0021 (4) | 0.0109 (3) | −0.0093 (3) |
O3 | 0.0206 (4) | 0.0210 (4) | 0.0244 (4) | −0.0007 (3) | 0.0024 (3) | −0.0035 (3) |
O4 | 0.0404 (5) | 0.0192 (4) | 0.0409 (4) | −0.0026 (4) | 0.0109 (4) | −0.0016 (4) |
O5 | 0.0405 (5) | 0.0349 (5) | 0.0274 (4) | −0.0059 (4) | 0.0029 (4) | −0.0090 (4) |
N1 | 0.0225 (5) | 0.0227 (5) | 0.0286 (5) | −0.0021 (4) | 0.0089 (4) | −0.0034 (4) |
C1 | 0.0205 (5) | 0.0201 (5) | 0.0205 (5) | −0.0012 (5) | 0.0047 (4) | −0.0025 (4) |
C2 | 0.0277 (6) | 0.0265 (6) | 0.0261 (5) | 0.0039 (5) | 0.0054 (5) | 0.0015 (5) |
C3 | 0.0247 (6) | 0.0303 (7) | 0.0379 (6) | 0.0083 (5) | 0.0045 (5) | −0.0014 (5) |
C4 | 0.0231 (6) | 0.0278 (6) | 0.0300 (6) | −0.0037 (5) | 0.0092 (5) | −0.0103 (5) |
C5 | 0.0261 (6) | 0.0357 (7) | 0.0230 (5) | −0.0027 (5) | 0.0065 (5) | 0.0008 (5) |
C6 | 0.0209 (5) | 0.0298 (6) | 0.0241 (5) | 0.0025 (5) | 0.0016 (4) | 0.0031 (4) |
C7 | 0.0274 (6) | 0.0471 (9) | 0.0468 (8) | −0.0064 (6) | 0.0178 (6) | −0.0139 (6) |
C8 | 0.0173 (5) | 0.0183 (5) | 0.0230 (5) | −0.0014 (4) | 0.0049 (4) | −0.0021 (4) |
C9 | 0.0232 (5) | 0.0204 (5) | 0.0226 (5) | 0.0012 (5) | 0.0056 (4) | 0.0024 (4) |
C10 | 0.0212 (5) | 0.0223 (6) | 0.0186 (5) | 0.0015 (5) | 0.0036 (4) | 0.0003 (4) |
C11 | 0.0183 (5) | 0.0197 (5) | 0.0239 (5) | −0.0019 (5) | 0.0065 (4) | −0.0028 (4) |
C12 | 0.0275 (6) | 0.0195 (5) | 0.0241 (5) | 0.0005 (5) | 0.0062 (4) | 0.0034 (4) |
C13 | 0.0273 (6) | 0.0237 (6) | 0.0200 (5) | −0.0013 (5) | 0.0039 (4) | 0.0008 (4) |
Geometric parameters (Å, º) top
S1—O2 | 1.4232 (8) | C5—C6 | 1.3825 (15) |
S1—O1 | 1.4288 (8) | C5—H5 | 0.9300 |
S1—O3 | 1.5935 (8) | C6—H6 | 0.9300 |
S1—C1 | 1.7556 (11) | C7—H7A | 0.9600 |
O3—C8 | 1.4119 (12) | C7—H7B | 0.9600 |
O4—N1 | 1.2304 (12) | C7—H7C | 0.9600 |
O5—N1 | 1.2282 (11) | C8—C9 | 1.3852 (14) |
N1—C11 | 1.4660 (13) | C8—C13 | 1.3874 (15) |
C1—C2 | 1.3855 (15) | C9—C10 | 1.3844 (15) |
C1—C6 | 1.3904 (15) | C9—H9 | 0.9300 |
C2—C3 | 1.3937 (16) | C10—C11 | 1.3850 (15) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C4 | 1.3907 (16) | C11—C12 | 1.3832 (14) |
C3—H3 | 0.9300 | C12—C13 | 1.3864 (15) |
C4—C5 | 1.3922 (16) | C12—H12 | 0.9300 |
C4—C7 | 1.5102 (15) | C13—H13 | 0.9300 |
| | | |
O2—S1—O1 | 119.64 (5) | C5—C6—H6 | 120.7 |
O2—S1—O3 | 102.82 (5) | C1—C6—H6 | 120.7 |
O1—S1—O3 | 110.36 (4) | C4—C7—H7A | 109.5 |
O2—S1—C1 | 110.05 (5) | C4—C7—H7B | 109.5 |
O1—S1—C1 | 109.03 (5) | H7A—C7—H7B | 109.5 |
O3—S1—C1 | 103.66 (4) | C4—C7—H7C | 109.5 |
C8—O3—S1 | 123.29 (7) | H7A—C7—H7C | 109.5 |
O5—N1—O4 | 123.53 (10) | H7B—C7—H7C | 109.5 |
O5—N1—C11 | 118.45 (9) | C9—C8—C13 | 122.66 (10) |
O4—N1—C11 | 118.02 (9) | C9—C8—O3 | 114.58 (9) |
C2—C1—C6 | 121.26 (10) | C13—C8—O3 | 122.53 (9) |
C2—C1—S1 | 119.50 (8) | C10—C9—C8 | 118.67 (10) |
C6—C1—S1 | 119.19 (9) | C10—C9—H9 | 120.7 |
C1—C2—C3 | 118.93 (10) | C8—C9—H9 | 120.7 |
C1—C2—H2 | 120.5 | C9—C10—C11 | 118.61 (9) |
C3—C2—H2 | 120.5 | C9—C10—H10 | 120.7 |
C4—C3—C2 | 120.96 (11) | C11—C10—H10 | 120.7 |
C4—C3—H3 | 119.5 | C12—C11—C10 | 122.83 (10) |
C2—C3—H3 | 119.5 | C12—C11—N1 | 118.51 (10) |
C3—C4—C5 | 118.56 (10) | C10—C11—N1 | 118.61 (9) |
C3—C4—C7 | 120.75 (11) | C11—C12—C13 | 118.62 (10) |
C5—C4—C7 | 120.69 (11) | C11—C12—H12 | 120.7 |
C6—C5—C4 | 121.59 (11) | C13—C12—H12 | 120.7 |
C6—C5—H5 | 119.2 | C12—C13—C8 | 118.56 (9) |
C4—C5—H5 | 119.2 | C12—C13—H13 | 120.7 |
C5—C6—C1 | 118.69 (11) | C8—C13—H13 | 120.7 |
| | | |
O2—S1—O3—C8 | 177.66 (7) | S1—C1—C6—C5 | 176.74 (9) |
O1—S1—O3—C8 | −53.62 (9) | S1—O3—C8—C9 | −138.45 (8) |
C1—S1—O3—C8 | 63.01 (8) | S1—O3—C8—C13 | 46.95 (13) |
O2—S1—C1—C2 | 122.94 (9) | C13—C8—C9—C10 | 2.38 (17) |
O1—S1—C1—C2 | −10.12 (11) | O3—C8—C9—C10 | −172.20 (10) |
O3—S1—C1—C2 | −127.67 (9) | C8—C9—C10—C11 | −1.53 (16) |
O2—S1—C1—C6 | −54.38 (10) | C9—C10—C11—C12 | −0.21 (17) |
O1—S1—C1—C6 | 172.55 (8) | C9—C10—C11—N1 | 177.06 (10) |
O3—S1—C1—C6 | 55.00 (10) | O5—N1—C11—C12 | 173.51 (10) |
C6—C1—C2—C3 | 1.39 (17) | O4—N1—C11—C12 | −5.89 (15) |
S1—C1—C2—C3 | −175.88 (8) | O5—N1—C11—C10 | −3.88 (15) |
C1—C2—C3—C4 | −1.18 (18) | O4—N1—C11—C10 | 176.72 (10) |
C2—C3—C4—C5 | 0.13 (18) | C10—C11—C12—C13 | 1.18 (17) |
C2—C3—C4—C7 | −179.84 (11) | N1—C11—C12—C13 | −176.09 (9) |
C3—C4—C5—C6 | 0.76 (18) | C11—C12—C13—C8 | −0.38 (16) |
C7—C4—C5—C6 | −179.27 (11) | C9—C8—C13—C12 | −1.41 (16) |
C4—C5—C6—C1 | −0.56 (18) | O3—C8—C13—C12 | 172.75 (10) |
C2—C1—C6—C5 | −0.54 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.54 | 2.9161 (14) | 105 |
C6—H6···O2 | 0.93 | 2.97 | 3.1474 (13) | 92 |
C6—H6···O3 | 0.93 | 2.87 | 3.1002 (14) | 95 |
C10—H10···O5 | 0.93 | 2.43 | 2.7187 (14) | 98 |
C12—H12···O4 | 0.93 | 2.42 | 2.7098 (14) | 98 |
C13—H13···O1 | 0.93 | 2.37 | 2.9907 (13) | 124 |
C3—H3···O2i | 0.93 | 2.64 | 3.5305 (15) | 162 |
C7—H7B···O2i | 0.96 | 3.00 | 3.8851 (17) | 155 |
C6—H6···O1ii | 0.93 | 2.86 | 3.3893 (13) | 117 |
C5—H5···O1ii | 0.93 | 2.63 | 3.2848 (14) | 128 |
C6—H6···O4iii | 0.93 | 2.69 | 3.5770 (15) | 159 |
C9—H9···O4iii | 0.93 | 2.53 | 3.3362 (14) | 146 |
C7—H7C···O1iv | 0.96 | 2.59 | 3.4696 (16) | 153 |
C10—H10···O5v | 0.93 | 2.50 | 3.2389 (13) | 137 |
C12—H12···O2vi | 0.93 | 2.59 | 3.4828 (13) | 161 |
C13—H13···O5vii | 0.93 | 2.90 | 3.2512 (14) | 104 |
C2—H2···Cgviii | 0.93 | 3.07 | 3.772 | 134 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+1/2; (v) −x+1, y+1/2, −z−1/2; (vi) x, y−1, z; (vii) x, −y−1/2, z+1/2; (viii) −x, y−1/2, −z+1/2. |