In the crystal structure of the title compound, C
13H
11NO
5S, the dihedral angle between the mean planes of the 4-tolyl and 2-nitrophenyl rings is 42.2 (2)°. There are weak C—H
O hydrogen bonds, which generate rings of graph-set motifs
S(5),
(4),
(5),
(6),
(6),
(7) and
(10). The supramolecular aggregation is completed by the presence of intermolecular van der Waals short contacts, and C—H
π and π–π interactions.
Supporting information
CCDC reference: 262466
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- R factor = 0.061
- wR factor = 0.187
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O4 .. 2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O5 .. 2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O4 .. 2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O5 .. 2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O3 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O3 .. 2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C .. O5 .. 2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O1 .. 2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. CG1 .. 3.08 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. O5 .. 3.79 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C13 H11 N O5 S
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 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 SCALEPAK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPAK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
2-Nitrophenyl 4-toluenesulfonate
top
Crystal data top
C13H11NO5S | F(000) = 608 |
Mr = 293.29 | Dx = 1.527 Mg m−3 |
Monoclinic, P21/a | Melting point = 354–355 K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.71073 Å |
a = 7.953 (1) Å | Cell parameters from 23615 reflections |
b = 20.468 (3) Å | θ = 2.5–27.4° |
c = 7.9450 (9) Å | µ = 0.27 mm−1 |
β = 99.516 (8)° | T = 150 K |
V = 1275.5 (3) Å3 | Fragment, colorless |
Z = 4 | 0.35 × 0.25 × 0.10 mm |
Data collection top
Nonius KappaCCD (with Oxford Cryostream) diffractometer | 2839 independent reflections |
Radiation source: fine-focus sealed tube | 1446 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans with κ offsets | θmax = 27.4°, θmin = 2.5° |
Absorption correction: multi-scan (HKL Scalepack; Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.902, Tmax = 0.973 | k = −26→25 |
3173 measured reflections | l = −10→10 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0948P)2] where P = (Fo2 + 2Fc2)/3 |
2839 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.41 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 | 0.98699 (13) | 0.39071 (5) | 0.26464 (12) | 0.0381 (3) | |
O1 | 0.9012 (4) | 0.45042 (13) | 0.2127 (3) | 0.0439 (7) | |
O2 | 0.9134 (4) | 0.34362 (14) | 0.3624 (3) | 0.0482 (8) | |
O3 | 1.1633 (3) | 0.40888 (13) | 0.3908 (3) | 0.0372 (7) | |
O4 | 1.5241 (4) | 0.37502 (15) | 0.1118 (3) | 0.0509 (8) | |
O5 | 1.4586 (4) | 0.34263 (14) | 0.3536 (4) | 0.0513 (8) | |
N1 | 1.4631 (4) | 0.38418 (17) | 0.2415 (4) | 0.0436 (9) | |
C1 | 1.0602 (5) | 0.35451 (19) | 0.0902 (4) | 0.0324 (9) | |
C2 | 1.1027 (5) | 0.28941 (19) | 0.0954 (5) | 0.0378 (10) | |
H2 | 1.0924 | 0.2643 | 0.1906 | 0.041 (4)* | |
C3 | 1.1613 (5) | 0.26157 (19) | −0.0436 (5) | 0.0373 (10) | |
H3 | 1.1877 | 0.2173 | −0.0419 | 0.041 (4)* | |
C4 | 1.1809 (5) | 0.29877 (19) | −0.1845 (4) | 0.0365 (10) | |
C5 | 1.1334 (5) | 0.3647 (2) | −0.1891 (5) | 0.0391 (10) | |
H5 | 1.1400 | 0.3895 | −0.2859 | 0.041 (4)* | |
C6 | 1.0761 (5) | 0.39359 (19) | −0.0492 (5) | 0.0369 (9) | |
H6 | 1.0494 | 0.4378 | −0.0497 | 0.041 (4)* | |
C7 | 1.2408 (6) | 0.2682 (2) | −0.3376 (5) | 0.0452 (11) | |
H7A | 1.3402 | 0.2421 | −0.3000 | 0.074 (9)* | |
H7B | 1.2683 | 0.3020 | −0.4123 | 0.074 (9)* | |
H7C | 1.1520 | 0.2412 | −0.3975 | 0.074 (9)* | |
C8 | 1.2597 (5) | 0.46111 (18) | 0.3440 (4) | 0.0318 (9) | |
C9 | 1.2156 (5) | 0.5245 (2) | 0.3777 (5) | 0.0417 (10) | |
H9 | 1.1212 | 0.5320 | 0.4303 | 0.041 (4)* | |
C10 | 1.3088 (5) | 0.5765 (2) | 0.3348 (5) | 0.0401 (10) | |
H10 | 1.2773 | 0.6188 | 0.3589 | 0.041 (4)* | |
C11 | 1.4476 (5) | 0.5667 (2) | 0.2572 (5) | 0.0419 (10) | |
H11 | 1.5078 | 0.6022 | 0.2246 | 0.041 (4)* | |
C12 | 1.4991 (5) | 0.5029 (2) | 0.2268 (5) | 0.0409 (10) | |
H12 | 1.5960 | 0.4955 | 0.1780 | 0.041 (4)* | |
C13 | 1.4028 (5) | 0.45072 (19) | 0.2708 (5) | 0.0366 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0398 (6) | 0.0387 (6) | 0.0381 (6) | −0.0001 (5) | 0.0134 (5) | −0.0003 (4) |
O1 | 0.0430 (17) | 0.0407 (18) | 0.0496 (16) | 0.0073 (14) | 0.0128 (14) | −0.0015 (13) |
O2 | 0.0560 (19) | 0.0469 (19) | 0.0479 (16) | −0.0094 (15) | 0.0263 (15) | 0.0021 (13) |
O3 | 0.0427 (16) | 0.0408 (17) | 0.0284 (13) | −0.0005 (13) | 0.0072 (12) | 0.0018 (11) |
O4 | 0.055 (2) | 0.057 (2) | 0.0425 (15) | 0.0059 (15) | 0.0130 (15) | −0.0111 (13) |
O5 | 0.065 (2) | 0.0386 (18) | 0.0519 (17) | 0.0092 (15) | 0.0128 (16) | 0.0046 (14) |
N1 | 0.050 (2) | 0.038 (2) | 0.044 (2) | 0.0054 (17) | 0.0126 (18) | −0.0018 (17) |
C1 | 0.031 (2) | 0.038 (2) | 0.0277 (18) | −0.0030 (18) | 0.0026 (16) | −0.0025 (17) |
C2 | 0.046 (3) | 0.032 (2) | 0.036 (2) | −0.0018 (19) | 0.0101 (19) | 0.0083 (17) |
C3 | 0.044 (2) | 0.030 (2) | 0.038 (2) | 0.0039 (19) | 0.0059 (19) | 0.0017 (17) |
C4 | 0.037 (2) | 0.036 (2) | 0.037 (2) | 0.0001 (19) | 0.0095 (18) | −0.0036 (17) |
C5 | 0.051 (3) | 0.033 (2) | 0.035 (2) | 0.004 (2) | 0.0155 (19) | 0.0067 (17) |
C6 | 0.046 (2) | 0.026 (2) | 0.040 (2) | 0.0027 (18) | 0.0101 (19) | 0.0028 (16) |
C7 | 0.060 (3) | 0.036 (3) | 0.044 (2) | −0.002 (2) | 0.022 (2) | −0.0056 (18) |
C8 | 0.036 (2) | 0.032 (2) | 0.0260 (18) | 0.0008 (18) | 0.0023 (17) | 0.0032 (15) |
C9 | 0.049 (3) | 0.042 (3) | 0.035 (2) | 0.006 (2) | 0.011 (2) | −0.0027 (18) |
C10 | 0.041 (2) | 0.033 (2) | 0.043 (2) | 0.003 (2) | −0.003 (2) | −0.0043 (18) |
C11 | 0.042 (3) | 0.040 (3) | 0.040 (2) | −0.002 (2) | −0.002 (2) | 0.0073 (18) |
C12 | 0.037 (2) | 0.046 (3) | 0.040 (2) | −0.004 (2) | 0.0077 (18) | −0.0039 (19) |
C13 | 0.045 (3) | 0.032 (2) | 0.0328 (19) | 0.0035 (19) | 0.0065 (19) | −0.0011 (16) |
Geometric parameters (Å, º) top
S1—O2 | 1.423 (3) | C5—C6 | 1.400 (5) |
S1—O1 | 1.427 (3) | C5—H5 | 0.9300 |
S1—O3 | 1.626 (3) | C6—H6 | 0.9300 |
S1—C1 | 1.754 (3) | C7—H7A | 0.9600 |
O3—C8 | 1.401 (4) | C7—H7B | 0.9600 |
O4—N1 | 1.224 (4) | C7—H7C | 0.9600 |
O5—N1 | 1.236 (4) | C8—C13 | 1.378 (5) |
N1—C13 | 1.475 (5) | C8—C9 | 1.381 (5) |
C1—C2 | 1.374 (5) | C9—C10 | 1.372 (5) |
C1—C6 | 1.389 (5) | C9—H9 | 0.9300 |
C2—C3 | 1.389 (5) | C10—C11 | 1.365 (5) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C4 | 1.384 (5) | C11—C12 | 1.402 (6) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.400 (5) | C12—C13 | 1.392 (5) |
C4—C7 | 1.512 (5) | C12—H12 | 0.9300 |
| | | |
O2—S1—O1 | 121.17 (17) | C1—C6—H6 | 120.8 |
O2—S1—O3 | 102.07 (16) | C5—C6—H6 | 120.8 |
O1—S1—O3 | 107.75 (16) | C4—C7—H7A | 109.5 |
O2—S1—C1 | 111.42 (18) | C4—C7—H7B | 109.5 |
O1—S1—C1 | 109.82 (17) | H7A—C7—H7B | 109.5 |
O3—S1—C1 | 102.62 (16) | C4—C7—H7C | 109.5 |
C8—O3—S1 | 117.7 (2) | H7A—C7—H7C | 109.5 |
O4—N1—O5 | 124.3 (3) | H7B—C7—H7C | 109.5 |
O4—N1—C13 | 117.3 (3) | C13—C8—C9 | 118.7 (4) |
O5—N1—C13 | 118.2 (3) | C13—C8—O3 | 121.4 (3) |
C2—C1—C6 | 121.9 (3) | C9—C8—O3 | 119.8 (3) |
C2—C1—S1 | 119.9 (3) | C10—C9—C8 | 121.0 (4) |
C6—C1—S1 | 118.2 (3) | C10—C9—H9 | 119.5 |
C1—C2—C3 | 119.2 (3) | C8—C9—H9 | 119.5 |
C1—C2—H2 | 120.4 | C11—C10—C9 | 120.6 (4) |
C3—C2—H2 | 120.4 | C11—C10—H10 | 119.7 |
C4—C3—C2 | 121.0 (4) | C9—C10—H10 | 119.7 |
C4—C3—H3 | 119.5 | C10—C11—C12 | 119.7 (4) |
C2—C3—H3 | 119.5 | C10—C11—H11 | 120.1 |
C3—C4—C5 | 119.0 (3) | C12—C11—H11 | 120.1 |
C3—C4—C7 | 121.0 (3) | C13—C12—C11 | 118.9 (4) |
C5—C4—C7 | 119.8 (3) | C13—C12—H12 | 120.6 |
C4—C5—C6 | 120.6 (3) | C11—C12—H12 | 120.6 |
C4—C5—H5 | 119.7 | C8—C13—C12 | 121.0 (4) |
C6—C5—H5 | 119.7 | C8—C13—N1 | 121.5 (3) |
C1—C6—C5 | 118.3 (4) | C12—C13—N1 | 117.5 (3) |
| | | |
O2—S1—O3—C8 | −171.8 (3) | C4—C5—C6—C1 | −3.0 (6) |
O1—S1—O3—C8 | −43.1 (3) | S1—O3—C8—C13 | −101.5 (4) |
C1—S1—O3—C8 | 72.7 (3) | S1—O3—C8—C9 | 81.2 (4) |
O2—S1—C1—C2 | −24.5 (4) | C13—C8—C9—C10 | 1.9 (6) |
O1—S1—C1—C2 | −161.6 (3) | O3—C8—C9—C10 | 179.3 (3) |
O3—S1—C1—C2 | 84.0 (3) | C8—C9—C10—C11 | 0.2 (6) |
O2—S1—C1—C6 | 156.6 (3) | C9—C10—C11—C12 | −2.4 (6) |
O1—S1—C1—C6 | 19.5 (4) | C10—C11—C12—C13 | 2.5 (6) |
O3—S1—C1—C6 | −94.9 (3) | C9—C8—C13—C12 | −1.8 (6) |
C6—C1—C2—C3 | −0.8 (6) | O3—C8—C13—C12 | −179.1 (3) |
S1—C1—C2—C3 | −179.7 (3) | C9—C8—C13—N1 | 176.1 (3) |
C1—C2—C3—C4 | 1.5 (6) | O3—C8—C13—N1 | −1.2 (5) |
C2—C3—C4—C5 | −2.9 (6) | C11—C12—C13—C8 | −0.4 (6) |
C2—C3—C4—C7 | −178.6 (4) | C11—C12—C13—N1 | −178.4 (3) |
C3—C4—C5—C6 | 3.6 (6) | O4—N1—C13—C8 | 143.6 (4) |
C7—C4—C5—C6 | 179.4 (4) | O5—N1—C13—C8 | −40.8 (5) |
C2—C1—C6—C5 | 1.6 (6) | O4—N1—C13—C12 | −38.4 (5) |
S1—C1—C6—C5 | −179.6 (3) | O5—N1—C13—C12 | 137.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.93 | 2.68 | 3.009 (5) | 102 |
C6—H6···O1 | 0.93 | 2.57 | 2.929 (4) | 103 |
C2—H2···O4i | 0.93 | 2.95 | 3.430 (5) | 114 |
C2—H2···O5i | 0.93 | 2.84 | 3.688 (5) | 153 |
C3—H3···O4i | 0.93 | 2.70 | 3.313 (5) | 124 |
C7—H7B···O5ii | 0.96 | 2.72 | 3.570 (5) | 149 |
C5—H5···O3ii | 0.93 | 2.64 | 3.504 (4) | 156 |
C7—H7B···O3ii | 0.96 | 2.74 | 3.590 (5) | 148 |
C6—H6···O1iii | 0.93 | 2.69 | 3.463 (5) | 141 |
C7—H7C···O5iv | 0.96 | 2.87 | 3.793 (5) | 163 |
C9—H9···O1v | 0.93 | 2.89 | 3.566 (4) | 130 |
C12—H12···O1vi | 0.93 | 2.57 | 3.392 (5) | 148 |
C7—H7A···Cg1vii | 0.96 | 3.08 | 3.99 | 158 |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x, y, z−1; (iii) −x+2, −y+1, −z; (iv) x−1/2, −y+1/2, z−1; (v) −x+2, −y+1, −z+1; (vi) x+1, y, z; (vii) x−1/2, −y−1/2, z. |