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The title compound, C7H7NO2S, forms centrosymmetric acid dimers which are connected through weak C—H...O interactions to form a tape. Adjacent tapes are arranged in a zigzag fashion with weak methyl–methyl interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005568/fl6150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005568/fl6150Isup2.hkl
Contains datablock I

CCDC reference: 270322

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.071
  • wR factor = 0.177
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.51 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.72 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2-(methylsulfanyl)nicotinic acid top
Crystal data top
C7H7NO2SF(000) = 352
Mr = 169.20Dx = 1.519 Mg m3
Monoclinic, P21/cMelting point: 489(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 3.9834 (10) ÅCell parameters from 1108 reflections
b = 25.373 (7) Åθ = 3.2–26.5°
c = 7.465 (2) ŵ = 0.38 mm1
β = 101.380 (4)°T = 298 K
V = 739.7 (3) Å3Plate, colourless
Z = 40.20 × 0.13 × 0.10 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
1462 independent reflections
Radiation source: fine-focus sealed tube1181 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 44
Tmin = 0.943, Tmax = 0.960k = 3128
4393 measured reflectionsl = 98
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0967P)2 + 0.4717P]
where P = (Fo2 + 2Fc2)/3
1462 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

Experimental. Crystals were grown by slow evaporation from CH2Cl2.

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
S10.3813 (2)0.34163 (4)0.37952 (12)0.0363 (3)
O10.1700 (7)0.44260 (11)0.4572 (3)0.0447 (8)
O20.2128 (8)0.49028 (13)0.2688 (4)0.0484 (8)
N10.1442 (9)0.33262 (12)0.0244 (4)0.0374 (8)
C20.0170 (9)0.41345 (14)0.1509 (4)0.0283 (8)
C30.1943 (10)0.42809 (16)0.0213 (5)0.0356 (9)
H30.31200.45990.03620.043*
C10.1507 (8)0.36425 (15)0.1674 (5)0.0288 (8)
C70.0112 (9)0.44975 (15)0.3054 (5)0.0312 (8)
C40.1972 (10)0.39582 (17)0.1699 (5)0.0420 (10)
H40.31020.40540.28650.050*
C60.5264 (11)0.27830 (17)0.3177 (6)0.0461 (10)
H6A0.33250.25590.27610.069*
H6B0.67110.26260.42220.069*
H6C0.65310.28260.22180.069*
C50.0258 (11)0.34893 (17)0.1380 (5)0.0417 (10)
H50.02830.32670.23740.050*
H10.186 (11)0.513 (2)0.344 (7)0.051 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0480 (6)0.0401 (6)0.0180 (5)0.0075 (4)0.0000 (4)0.0011 (4)
O10.0633 (18)0.0444 (17)0.0202 (14)0.0153 (13)0.0073 (12)0.0057 (12)
O20.071 (2)0.0419 (18)0.0255 (15)0.0182 (15)0.0063 (13)0.0086 (14)
N10.0540 (19)0.0360 (18)0.0199 (16)0.0003 (14)0.0019 (14)0.0062 (13)
C20.0371 (18)0.034 (2)0.0132 (17)0.0007 (14)0.0023 (13)0.0014 (14)
C30.047 (2)0.037 (2)0.0196 (18)0.0013 (16)0.0004 (15)0.0025 (16)
C10.0337 (18)0.037 (2)0.0161 (16)0.0041 (15)0.0052 (13)0.0009 (15)
C70.0426 (19)0.034 (2)0.0159 (17)0.0007 (15)0.0039 (14)0.0006 (14)
C40.054 (2)0.049 (3)0.0198 (19)0.0002 (19)0.0010 (16)0.0010 (17)
C60.055 (2)0.039 (2)0.042 (2)0.0115 (19)0.0047 (19)0.0025 (19)
C50.057 (2)0.045 (2)0.021 (2)0.0027 (19)0.0026 (17)0.0090 (17)
Geometric parameters (Å, º) top
S1—C11.763 (4)C2—C71.473 (5)
S1—C61.798 (4)C3—C41.378 (6)
O1—C71.231 (4)C3—H30.9300
O2—C71.300 (4)C4—C51.369 (6)
O2—H10.79 (5)C4—H40.9300
N1—C11.332 (5)C6—H6A0.9600
N1—C51.332 (5)C6—H6B0.9600
C2—C31.389 (5)C6—H6C0.9600
C2—C11.410 (5)C5—H50.9300
C1—S1—C6101.38 (19)O2—C7—C2114.6 (3)
C7—O2—H1115 (3)C5—C4—C3116.8 (4)
C1—N1—C5117.9 (3)C5—C4—H4121.6
C3—C2—C1117.6 (3)C3—C4—H4121.6
C3—C2—C7118.9 (3)S1—C6—H6A109.5
C1—C2—C7123.5 (3)S1—C6—H6B109.5
C4—C3—C2120.6 (4)H6A—C6—H6B109.5
C4—C3—H3119.7S1—C6—H6C109.5
C2—C3—H3119.7H6A—C6—H6C109.5
N1—C1—C2122.0 (3)H6B—C6—H6C109.5
N1—C1—S1116.6 (3)N1—C5—C4125.1 (4)
C2—C1—S1121.4 (3)N1—C5—H5117.5
O1—C7—O2122.4 (3)C4—C5—H5117.5
O1—C7—C2123.0 (3)
 

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