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In the mol­ecule of the title compound, C13H11NO6S, an intra­molecular O—H...O hydrogen bond is formed between the hydr­oxy group and the nitro O atom. The two aromatic rings form a dihedral angle of 48.8 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002406/hk6079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002406/hk6079Isup2.hkl
Contains datablock I

CCDC reference: 298469

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.136
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.03 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 390 Refinement of F2^ against ALL reflections. The weighted R-factor wR and If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 391 goodness of fit S are based on F2^, conventional R-factors R are based If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 392 on F, with F set to zero for negative F2^. The threshold expression of If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 395 on F2^ are statistically about twice as large as those based on F, and R- If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 404 'w = 1/[\s2^(Fo2^)+(0.0679P)2^+0.8662P] where P=(Fo2^+2Fc2^)/3' If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
5 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-Hydroxy-4-nitrophenyl 4-toluenesulfonate top
Crystal data top
C13H11NO6SDx = 1.485 Mg m3
Mr = 309.30Melting point: 361 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3444 reflections
a = 6.2331 (9) Åθ = 2.6–23.8°
b = 16.000 (2) ŵ = 0.26 mm1
c = 27.741 (4) ÅT = 294 K
V = 2766.6 (7) Å3Block, colourless
Z = 80.26 × 0.24 × 0.12 mm
F(000) = 1280
Data collection top
Bruker 1000 CCD area-detector
diffractometer
2830 independent reflections
Radiation source: fine-focus sealed tube1547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.935, Tmax = 0.969k = 1919
14390 measured reflectionsl = 3417
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.8662P]
where P = (Fo2 + 2Fc2)/3
2830 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.23 e Å3
12 restraintsΔρmin = 0.30 e Å3
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
S10.24533 (11)0.53721 (4)0.16281 (2)0.0527 (2)
O10.4535 (3)0.55580 (12)0.14504 (7)0.0673 (5)
O20.2171 (4)0.47795 (12)0.20009 (7)0.0760 (6)
O30.1081 (3)0.49767 (10)0.11896 (6)0.0580 (5)
O40.3660 (3)0.60083 (17)0.02989 (8)0.0889 (7)
H40.33030.62950.05300.133*
O50.1007 (5)0.69237 (17)0.07802 (8)0.1012 (8)
O60.2130 (5)0.72121 (18)0.04984 (10)0.1190 (10)
N10.0392 (5)0.68604 (18)0.04673 (10)0.0779 (7)
C10.1076 (4)0.62943 (14)0.17497 (8)0.0419 (6)
C20.1914 (4)0.70479 (15)0.15977 (9)0.0509 (6)
H20.32420.70690.14450.061*
C30.0757 (5)0.77672 (16)0.16751 (9)0.0584 (7)
H30.13230.82760.15750.070*
C40.1229 (4)0.77533 (16)0.18985 (9)0.0535 (7)
C50.2023 (4)0.69885 (17)0.20520 (9)0.0543 (7)
H50.33480.69690.22060.065*
C60.0894 (4)0.62558 (16)0.19820 (9)0.0503 (6)
H60.14420.57470.20880.060*
C70.2495 (6)0.85419 (19)0.19764 (12)0.0813 (10)
H7A0.22860.87350.23010.122*
H7B0.39900.84320.19240.122*
H7C0.20160.89630.17540.122*
C80.0791 (4)0.54601 (14)0.07732 (9)0.0487 (6)
C90.1193 (4)0.58438 (18)0.07118 (10)0.0597 (7)
H90.22590.57960.09450.072*
C100.1533 (4)0.62911 (19)0.03021 (11)0.0637 (8)
H100.28520.65490.02520.076*
C110.0052 (5)0.63660 (16)0.00393 (10)0.0559 (7)
C120.2037 (4)0.59743 (18)0.00205 (10)0.0572 (7)
C130.2378 (4)0.55128 (16)0.04362 (10)0.0550 (7)
H130.36790.52410.04850.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0503 (4)0.0493 (4)0.0583 (4)0.0026 (3)0.0015 (3)0.0045 (3)
O10.0434 (10)0.0768 (13)0.0815 (13)0.0031 (9)0.0042 (10)0.0001 (11)
O20.0905 (15)0.0606 (12)0.0770 (13)0.0106 (11)0.0018 (12)0.0236 (11)
O30.0640 (11)0.0453 (10)0.0647 (11)0.0078 (9)0.0043 (9)0.0063 (9)
O40.0628 (13)0.129 (2)0.0754 (15)0.0072 (13)0.0163 (12)0.0107 (14)
O50.111 (2)0.123 (2)0.0695 (14)0.0054 (17)0.0011 (15)0.0108 (14)
O60.122 (2)0.134 (2)0.1013 (19)0.0520 (19)0.0160 (17)0.0158 (17)
N10.090 (2)0.0789 (18)0.0648 (17)0.0025 (16)0.0107 (17)0.0103 (15)
C10.0430 (13)0.0440 (13)0.0388 (12)0.0043 (10)0.0004 (10)0.0004 (10)
C20.0493 (14)0.0506 (15)0.0528 (14)0.0074 (11)0.0113 (12)0.0004 (12)
C30.0708 (18)0.0427 (14)0.0617 (16)0.0087 (13)0.0079 (15)0.0002 (12)
C40.0611 (18)0.0555 (16)0.0439 (14)0.0046 (13)0.0046 (13)0.0116 (12)
C50.0456 (14)0.0711 (18)0.0462 (14)0.0021 (13)0.0068 (12)0.0082 (13)
C60.0492 (14)0.0539 (15)0.0477 (14)0.0092 (12)0.0031 (12)0.0021 (12)
C70.095 (2)0.0711 (19)0.078 (2)0.0217 (18)0.0003 (19)0.0188 (17)
C80.0485 (14)0.0436 (13)0.0541 (15)0.0014 (11)0.0015 (12)0.0173 (12)
C90.0441 (15)0.0787 (19)0.0563 (16)0.0018 (13)0.0037 (13)0.0197 (15)
C100.0492 (16)0.0773 (19)0.0646 (18)0.0149 (14)0.0069 (15)0.0245 (16)
C110.0603 (16)0.0555 (15)0.0520 (15)0.0014 (13)0.0087 (14)0.0148 (13)
C120.0494 (16)0.0682 (17)0.0542 (15)0.0033 (13)0.0068 (13)0.0156 (14)
C130.0431 (14)0.0583 (16)0.0637 (16)0.0054 (12)0.0044 (13)0.0146 (13)
Geometric parameters (Å, º) top
S1—O21.4142 (19)C4—C71.504 (4)
S1—O11.4195 (19)C5—C61.381 (4)
S1—O31.6160 (18)C5—H50.9300
S1—C11.740 (2)C6—H60.9300
O3—C81.402 (3)C7—H7A0.9600
O4—C121.346 (3)C7—H7B0.9600
O4—H40.8200C7—H7C0.9600
O5—N11.234 (3)C8—C131.364 (3)
O6—N11.224 (4)C8—C91.391 (4)
N1—C111.453 (4)C9—C101.360 (4)
C1—C21.380 (3)C9—H90.9300
C1—C61.388 (3)C10—C111.374 (4)
C2—C31.375 (3)C10—H100.9300
C2—H20.9300C11—C121.397 (4)
C3—C41.385 (4)C12—C131.386 (4)
C3—H30.9300C13—H130.9300
C4—C51.387 (4)
O2—S1—O1120.55 (12)C5—C6—H6120.7
O2—S1—O3102.84 (11)C1—C6—H6120.7
O1—S1—O3107.73 (11)C4—C7—H7A109.5
O2—S1—C1111.42 (12)C4—C7—H7B109.5
O1—S1—C1109.92 (12)H7A—C7—H7B109.5
O3—S1—C1102.52 (10)C4—C7—H7C109.5
C8—O3—S1118.20 (14)H7A—C7—H7C109.5
C12—O4—H4109.5H7B—C7—H7C109.5
O6—N1—O5122.5 (3)C13—C8—C9122.2 (3)
O6—N1—C11118.5 (3)C13—C8—O3120.4 (2)
O5—N1—C11119.0 (3)C9—C8—O3117.3 (2)
C2—C1—C6121.0 (2)C10—C9—C8118.2 (3)
C2—C1—S1119.64 (19)C10—C9—H9120.9
C6—C1—S1119.27 (18)C8—C9—H9120.9
C3—C2—C1119.0 (2)C9—C10—C11120.7 (3)
C3—C2—H2120.5C9—C10—H10119.7
C1—C2—H2120.5C11—C10—H10119.7
C2—C3—C4121.7 (2)C10—C11—C12121.1 (3)
C2—C3—H3119.2C10—C11—N1118.3 (3)
C4—C3—H3119.2C12—C11—N1120.7 (3)
C3—C4—C5118.1 (2)O4—C12—C13117.0 (2)
C3—C4—C7121.3 (3)O4—C12—C11124.7 (3)
C5—C4—C7120.6 (3)C13—C12—C11118.3 (2)
C6—C5—C4121.6 (2)C8—C13—C12119.5 (2)
C6—C5—H5119.2C8—C13—H13120.3
C4—C5—H5119.2C12—C13—H13120.3
C5—C6—C1118.6 (2)
O2—S1—O3—C8172.30 (18)S1—O3—C8—C1380.1 (2)
O1—S1—O3—C859.37 (19)S1—O3—C8—C9102.8 (2)
C1—S1—O3—C856.56 (18)C13—C8—C9—C100.6 (4)
O2—S1—C1—C2146.6 (2)O3—C8—C9—C10177.7 (2)
O1—S1—C1—C210.3 (2)C8—C9—C10—C110.5 (4)
O3—S1—C1—C2104.0 (2)C9—C10—C11—C121.1 (4)
O2—S1—C1—C635.9 (2)C9—C10—C11—N1179.2 (2)
O1—S1—C1—C6172.17 (18)O6—N1—C11—C102.4 (4)
O3—S1—C1—C673.5 (2)O5—N1—C11—C10179.0 (3)
C6—C1—C2—C30.6 (4)O6—N1—C11—C12178.0 (3)
S1—C1—C2—C3176.8 (2)O5—N1—C11—C120.6 (4)
C1—C2—C3—C40.4 (4)C10—C11—C12—O4179.2 (3)
C2—C3—C4—C51.0 (4)N1—C11—C12—O40.5 (4)
C2—C3—C4—C7179.3 (3)C10—C11—C12—C130.6 (4)
C3—C4—C5—C60.7 (4)N1—C11—C12—C13179.8 (2)
C7—C4—C5—C6179.6 (2)C9—C8—C13—C121.1 (4)
C4—C5—C6—C10.3 (4)O3—C8—C13—C12178.2 (2)
C2—C1—C6—C51.0 (4)O4—C12—C13—C8179.7 (2)
S1—C1—C6—C5176.44 (19)C11—C12—C13—C80.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O50.821.882.581 (3)143
O4—H4···N10.822.482.908 (4)114
 

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