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In the title compound, C12H9NO6S, the two aromatic rings form a dihedral angle of 50.0 (2)°. An inter­molecular O—H...O hydrogen bond is formed between the hydr­oxy group and the sulfonyl O atom of an adjacent mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002121/ww6474sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002121/ww6474Isup2.hkl
Contains datablock I

CCDC reference: 298577

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.096
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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.

4-Hydroxy-3-nitrophenyl benzenesulfonate top
Crystal data top
C12H9NO6SZ = 2
Mr = 295.27F(000) = 304
Triclinic, P1Dx = 1.574 Mg m3
Hall symbol: -P 1Melting point: 343 K
a = 6.1372 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.7339 (13) ÅCell parameters from 1923 reflections
c = 13.152 (2) Åθ = 2.6–28.0°
α = 87.833 (2)°µ = 0.29 mm1
β = 89.884 (2)°T = 293 K
γ = 87.135 (2)°Block, colourless
V = 623.03 (18) Å30.24 × 0.22 × 0.18 mm
Data collection top
Bruker SMART CD area-detector
diffractometer
2192 independent reflections
Radiation source: fine-focus sealed tube1853 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 57
Tmin = 0.934, Tmax = 0.950k = 99
3245 measured reflectionsl = 1415
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.1779P]
where P = (Fo2 + 2Fc2)/3
2138 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.44 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 > 2σ(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
S10.37630 (9)0.48273 (6)0.67459 (3)0.04613 (18)
O10.3592 (2)0.31126 (16)0.61230 (9)0.0428 (3)
O20.1736 (3)0.57831 (17)0.66920 (11)0.0645 (4)
O30.5687 (3)0.5547 (2)0.63573 (11)0.0690 (5)
N10.0454 (3)0.1334 (2)0.78211 (12)0.0474 (4)
O40.0953 (3)0.1435 (2)0.84732 (12)0.0723 (5)
O50.2016 (3)0.2267 (2)0.78486 (12)0.0666 (4)
O60.3734 (2)0.07351 (18)0.62102 (12)0.0561 (4)
H60.360 (4)0.155 (3)0.6633 (16)0.084*
C10.1683 (3)0.2179 (2)0.62139 (12)0.0354 (4)
C20.1538 (3)0.0917 (2)0.69597 (13)0.0372 (4)
H20.26460.07150.74380.045*
C30.0299 (3)0.0060 (2)0.69893 (12)0.0361 (4)
C40.1955 (3)0.0194 (2)0.62623 (14)0.0383 (4)
C50.1744 (3)0.1515 (2)0.55227 (14)0.0415 (4)
H5A0.28400.17320.50400.050*
C60.0048 (3)0.2498 (2)0.54954 (13)0.0397 (4)
H6A0.01690.33740.49980.048*
C70.4205 (3)0.4010 (2)0.79931 (13)0.0415 (4)
C80.2514 (3)0.4063 (3)0.86846 (15)0.0509 (5)
H80.11690.45980.85100.061*
C90.2861 (4)0.3304 (3)0.96425 (17)0.0640 (6)
H90.17410.33291.01200.077*
C100.4846 (4)0.2516 (3)0.98929 (17)0.0676 (7)
H100.50590.20001.05370.081*
C110.6530 (4)0.2483 (3)0.91971 (19)0.0681 (6)
H110.78730.19460.93740.082*
C120.6223 (3)0.3244 (3)0.82394 (16)0.0541 (5)
H120.73550.32420.77680.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0643 (4)0.0346 (3)0.0402 (3)0.0134 (2)0.0088 (2)0.00391 (18)
O10.0460 (7)0.0430 (7)0.0408 (7)0.0140 (6)0.0017 (5)0.0031 (5)
O20.0909 (12)0.0448 (8)0.0564 (9)0.0114 (8)0.0209 (8)0.0019 (6)
O30.0921 (12)0.0631 (9)0.0553 (9)0.0463 (9)0.0022 (8)0.0082 (7)
N10.0610 (10)0.0425 (9)0.0391 (9)0.0110 (8)0.0012 (8)0.0038 (7)
O40.0915 (12)0.0718 (10)0.0537 (9)0.0254 (9)0.0268 (9)0.0247 (8)
O50.0777 (11)0.0674 (10)0.0568 (9)0.0346 (9)0.0007 (8)0.0135 (7)
O60.0467 (8)0.0528 (8)0.0697 (10)0.0160 (7)0.0106 (7)0.0060 (7)
C10.0401 (10)0.0318 (8)0.0348 (9)0.0053 (7)0.0008 (7)0.0025 (7)
C20.0405 (10)0.0369 (9)0.0344 (9)0.0018 (7)0.0053 (7)0.0026 (7)
C30.0434 (10)0.0316 (8)0.0332 (9)0.0033 (7)0.0014 (7)0.0007 (7)
C40.0359 (10)0.0356 (9)0.0438 (10)0.0031 (7)0.0001 (8)0.0060 (7)
C50.0439 (11)0.0384 (9)0.0420 (10)0.0012 (8)0.0108 (8)0.0017 (8)
C60.0526 (11)0.0318 (8)0.0344 (9)0.0022 (8)0.0034 (8)0.0014 (7)
C70.0523 (11)0.0358 (9)0.0373 (9)0.0103 (8)0.0074 (8)0.0001 (7)
C80.0523 (12)0.0514 (11)0.0493 (11)0.0072 (9)0.0019 (9)0.0010 (9)
C90.0747 (16)0.0718 (14)0.0463 (12)0.0166 (12)0.0036 (11)0.0049 (10)
C100.0916 (19)0.0674 (14)0.0440 (12)0.0164 (13)0.0169 (12)0.0124 (10)
C110.0714 (16)0.0686 (14)0.0633 (15)0.0026 (12)0.0265 (12)0.0034 (11)
C120.0525 (12)0.0600 (12)0.0499 (11)0.0037 (10)0.0080 (9)0.0041 (9)
Geometric parameters (Å, º) top
S1—O21.4153 (16)C4—C51.395 (2)
S1—O31.4164 (15)C5—C61.367 (2)
S1—O11.5928 (13)C5—H5A0.9300
S1—C71.7522 (18)C6—H6A0.9300
O1—C11.409 (2)C7—C81.379 (3)
N1—O41.216 (2)C7—C121.379 (3)
N1—O51.228 (2)C8—C91.382 (3)
N1—C31.451 (2)C8—H80.9300
O6—C41.340 (2)C9—C101.369 (3)
O6—H60.825 (10)C9—H90.9300
C1—C21.364 (2)C10—C111.379 (4)
C1—C61.386 (3)C10—H100.9300
C2—C31.388 (2)C11—C121.379 (3)
C2—H20.9300C11—H110.9300
C3—C41.398 (3)C12—H120.9300
O2—S1—O3120.81 (10)C6—C5—H5A119.5
O2—S1—O1108.90 (8)C4—C5—H5A119.5
O3—S1—O1103.26 (8)C5—C6—C1119.61 (16)
O2—S1—C7109.52 (9)C5—C6—H6A120.2
O3—S1—C7110.00 (9)C1—C6—H6A120.2
O1—S1—C7102.67 (8)C8—C7—C12121.72 (18)
C1—O1—S1118.81 (10)C8—C7—S1119.66 (15)
O4—N1—O5122.08 (16)C12—C7—S1118.53 (15)
O4—N1—C3119.09 (16)C7—C8—C9118.6 (2)
O5—N1—C3118.82 (16)C7—C8—H8120.7
C4—O6—H6108 (2)C9—C8—H8120.7
C2—C1—C6121.52 (16)C10—C9—C8120.4 (2)
C2—C1—O1119.72 (15)C10—C9—H9119.8
C6—C1—O1118.62 (15)C8—C9—H9119.8
C1—C2—C3118.47 (16)C9—C10—C11120.5 (2)
C1—C2—H2120.8C9—C10—H10119.7
C3—C2—H2120.8C11—C10—H10119.7
C2—C3—C4121.62 (16)C10—C11—C12120.0 (2)
C2—C3—N1117.12 (16)C10—C11—H11120.0
C4—C3—N1121.25 (16)C12—C11—H11120.0
O6—C4—C5116.83 (16)C7—C12—C11118.8 (2)
O6—C4—C3125.48 (16)C7—C12—H12120.6
C5—C4—C3117.69 (16)C11—C12—H12120.6
C6—C5—C4121.05 (17)
O2—S1—O1—C141.73 (14)C3—C4—C5—C61.6 (3)
O3—S1—O1—C1171.29 (12)C4—C5—C6—C10.1 (3)
C7—S1—O1—C174.30 (13)C2—C1—C6—C50.8 (3)
S1—O1—C1—C289.09 (17)O1—C1—C6—C5174.98 (14)
S1—O1—C1—C695.08 (16)O2—S1—C7—C812.27 (18)
C6—C1—C2—C30.0 (3)O3—S1—C7—C8147.29 (16)
O1—C1—C2—C3175.74 (14)O1—S1—C7—C8103.32 (16)
C1—C2—C3—C41.7 (3)O2—S1—C7—C12171.10 (15)
C1—C2—C3—N1177.03 (15)O3—S1—C7—C1236.08 (18)
O4—N1—C3—C23.5 (3)O1—S1—C7—C1273.31 (16)
O5—N1—C3—C2177.21 (16)C12—C7—C8—C90.9 (3)
O4—N1—C3—C4175.26 (17)S1—C7—C8—C9175.63 (15)
O5—N1—C3—C44.1 (3)C7—C8—C9—C100.1 (3)
C2—C3—C4—O6177.14 (16)C8—C9—C10—C110.6 (4)
N1—C3—C4—O64.2 (3)C9—C10—C11—C120.1 (4)
C2—C3—C4—C52.5 (3)C8—C7—C12—C111.4 (3)
N1—C3—C4—C5176.20 (15)S1—C7—C12—C11175.17 (16)
O6—C4—C5—C6178.01 (16)C10—C11—C12—C70.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O50.83 (1)1.92 (2)2.617 (2)141 (3)
O6—H6···O3i0.83 (1)2.35 (2)2.914 (2)126 (2)
Symmetry code: (i) x1, y1, z.
 

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