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The title tetra­gonal polymorph is one of the two sulfathia­zole–pyridine adducts, C9H9N3O2S2·C5H5N, that can be formed either by crystallization from an n-propanol–pyridine solution, or by exposure of solid sulfathia­zole to pyridine vapour. The asymmetric unit consists of a hydrogen-bonded sulfathia­zole–pyridine pair. Hydrogen bonds of the form Naniline—H...Osulfonyl form a three-dimensional network. Pyridine mol­ecules linked to sulfathia­zole mol­ecules by Namino—H...Npyridine hydrogen bonds are located in the channels of the sulfathia­zole framework which extend along the 41 axis. The angle between neighbouring pyridine rings in the channels is 55.2 (3)°. The adduct is stable in pyridine vapour, but decomposes in air under ambient conditions, giving the metastable polymorph I of sulfathia­zole [Kruger & Gafner (1972). Acta Cryst. B28, 272–283].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020101/cv2061sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020101/cv2061Isup2.hkl
Contains datablock I

CCDC reference: 613647

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.064
  • wR factor = 0.132
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 13
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.310 From the CIF: _refine_ls_abs_structure_Flack_su 0.170 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.31 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C11 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 25.49 From the CIF: _reflns_number_total 2518 From the CIF: _diffrn_reflns_limit_ max hkl 7. 10. 25. From the CIF: _diffrn_reflns_limit_ min hkl -7. -9. -22. TEST1: Expected hkl limits for theta max Calculated maximum hkl 10. 10. 25. Calculated minimum hkl -10. -10. -25. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.49 From the CIF: _reflns_number_total 2518 Count of symmetry unique reflns 1512 Completeness (_total/calc) 166.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1006 Fraction of Friedel pairs measured 0.665 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and PowderCell (Kraus & Nolze, 1999); software used to prepare material for publication: SHELXL97.

sulfathiazole–pyridine (1/1) top
Crystal data top
C9H9N3O2S2·C5H5NDx = 1.412 Mg m3
Mr = 334.43Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 69 reflections
Hall symbol: P 4wθ = 10.1–14.6°
a = 8.670 (2) ŵ = 0.35 mm1
c = 20.927 (10) ÅT = 295 K
V = 1573.2 (9) Å3Pyramid, colourless
Z = 40.46 × 0.41 × 0.38 mm
F(000) = 696
Data collection top
Stoe STADI-4 four-circle D094
diffractometer
1726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Planar graphite monochromatorθmax = 25.5°, θmin = 2.4°
Scan width (ω) = 2.20–2.40, scan ratio 2θ:θ = 1.00 I(Net) and σ(I) calculated according to Blessing (1987)h = 77
Absorption correction: ψ scan
(X-RED; Stoe & Cie, 1997)
k = 910
Tmin = 0.771, Tmax = 0.874l = 2225
2518 measured reflections3 standard reflections every 180 min
2518 independent reflections intensity decay: 38.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.03P)2 + 1.3187P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
2518 reflectionsΔρmax = 0.23 e Å3
205 parametersΔρmin = 0.28 e Å3
1 restraintAbsolute structure: Flack (1983), with 1006 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.31 (17)
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
C11.3987 (8)0.9982 (8)1.0027 (3)0.0443 (18)
C21.3779 (8)0.9368 (8)1.0632 (4)0.0482 (18)
H31.46260.92301.08990.058*
C31.2334 (8)0.8962 (7)1.0842 (3)0.0399 (18)
H41.22130.85451.12490.048*
C41.1060 (7)0.9164 (7)1.0457 (3)0.0354 (16)
C51.1249 (8)0.9763 (8)0.9843 (3)0.0393 (17)
H51.04030.98750.95740.047*
C61.2697 (8)1.0186 (8)0.9639 (3)0.0458 (19)
H61.28171.06150.92350.055*
C70.9290 (8)0.5987 (9)1.0216 (3)0.0441 (18)
C81.0724 (12)0.3522 (10)1.0288 (5)0.079 (3)
H81.13720.26931.03750.095*
C90.9600 (11)0.3493 (10)0.9867 (4)0.071 (3)
H90.93670.26300.96210.085*
C100.5010 (14)0.6091 (11)0.9410 (5)0.081 (3)
H100.545 (9)0.699 (10)0.969 (4)0.08 (3)*
C110.3512 (15)0.6119 (14)0.9260 (7)0.111 (4)
H110.28470.68350.94440.133*
C120.2994 (13)0.5063 (18)0.8829 (7)0.108 (4)
H120.19690.50630.86970.130*
C130.4001 (14)0.4017 (15)0.8596 (6)0.118 (4)
H130.36770.32550.83130.141*
C140.5481 (12)0.4100 (13)0.8782 (6)0.100 (4)
H140.61700.33870.86130.120*
N11.5415 (8)1.0414 (9)0.9827 (3)0.075 (2)
H11.61951.03071.00760.06 (3)*
H21.55371.07940.94510.06 (3)*
N20.8590 (6)0.7341 (6)1.0226 (3)0.0420 (14)
N30.8803 (8)0.4852 (7)0.9826 (3)0.0569 (17)
H70.80420.49730.95670.068*
N40.6015 (8)0.5116 (8)0.9186 (3)0.065 (2)
O10.8184 (5)0.9919 (5)1.0642 (3)0.0573 (14)
O20.9366 (6)0.8013 (5)1.1356 (2)0.0492 (13)
S10.9210 (2)0.86308 (19)1.07180 (10)0.0420 (4)
S21.0846 (3)0.5297 (2)1.06594 (11)0.0626 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.036 (4)0.054 (5)0.043 (5)0.003 (4)0.003 (4)0.000 (4)
C20.045 (4)0.053 (4)0.047 (5)0.004 (3)0.013 (4)0.003 (4)
C30.048 (5)0.037 (4)0.035 (4)0.002 (3)0.005 (4)0.005 (3)
C40.035 (4)0.033 (4)0.038 (4)0.003 (3)0.006 (3)0.011 (3)
C50.047 (4)0.041 (4)0.029 (4)0.004 (3)0.005 (4)0.004 (3)
C60.039 (4)0.054 (5)0.045 (4)0.004 (4)0.003 (4)0.003 (4)
C70.048 (4)0.047 (5)0.037 (4)0.010 (4)0.005 (4)0.004 (4)
C80.112 (8)0.048 (5)0.077 (6)0.023 (5)0.018 (6)0.015 (5)
C90.101 (7)0.045 (5)0.067 (6)0.003 (5)0.016 (6)0.015 (5)
C100.104 (9)0.056 (7)0.082 (8)0.002 (7)0.000 (7)0.023 (6)
C110.081 (9)0.102 (10)0.150 (12)0.035 (7)0.018 (9)0.010 (9)
C120.055 (7)0.147 (12)0.124 (11)0.015 (8)0.021 (7)0.032 (9)
C130.082 (9)0.146 (11)0.125 (10)0.009 (8)0.039 (7)0.073 (9)
C140.070 (7)0.111 (9)0.120 (9)0.022 (6)0.003 (7)0.065 (8)
N10.050 (5)0.124 (7)0.050 (5)0.020 (4)0.000 (4)0.008 (5)
N20.049 (4)0.036 (4)0.041 (3)0.005 (3)0.006 (3)0.009 (3)
N30.076 (5)0.049 (4)0.046 (4)0.011 (4)0.012 (4)0.008 (3)
N40.069 (5)0.058 (5)0.068 (5)0.001 (4)0.008 (4)0.021 (4)
O10.044 (3)0.050 (3)0.078 (4)0.013 (2)0.002 (3)0.008 (3)
O20.065 (4)0.045 (3)0.038 (3)0.007 (3)0.006 (3)0.001 (2)
S10.0418 (10)0.0385 (10)0.0459 (10)0.0012 (9)0.0007 (10)0.0049 (10)
S20.0812 (15)0.0457 (11)0.0610 (13)0.0084 (10)0.0203 (13)0.0111 (12)
Geometric parameters (Å, º) top
C1—N11.360 (9)C9—H90.9300
C1—C21.386 (10)C10—N41.302 (11)
C1—C61.393 (9)C10—C111.336 (15)
C2—C31.374 (9)C10—H101.04 (9)
C2—H30.9300C11—C121.362 (15)
C3—C41.379 (8)C11—H110.9300
C3—H40.9300C12—C131.350 (15)
C4—C51.395 (9)C12—H120.9300
C4—S11.757 (6)C13—C141.343 (13)
C5—C61.376 (9)C13—H130.9300
C5—H50.9300C14—N41.305 (11)
C6—H60.9300C14—H140.9300
C7—N21.321 (8)N1—H10.8600
C7—N31.346 (8)N1—H20.8600
C7—S21.744 (8)N2—S11.613 (6)
C8—C91.314 (11)N3—H70.8600
C8—S21.727 (8)O1—S11.437 (4)
C8—H80.9300O2—S11.444 (5)
C9—N31.369 (10)
N1—C1—C2120.4 (7)C11—C10—H10118 (4)
N1—C1—C6121.1 (7)C10—C11—C12117.6 (11)
C2—C1—C6118.5 (7)C10—C11—H11121.2
C3—C2—C1120.6 (7)C12—C11—H11121.2
C3—C2—H3119.7C13—C12—C11118.5 (11)
C1—C2—H3119.7C13—C12—H12120.8
C2—C3—C4120.7 (6)C11—C12—H12120.8
C2—C3—H4119.6C14—C13—C12118.5 (11)
C4—C3—H4119.6C14—C13—H13120.8
C3—C4—C5119.5 (6)C12—C13—H13120.8
C3—C4—S1121.0 (5)N4—C14—C13124.3 (9)
C5—C4—S1119.5 (5)N4—C14—H14117.9
C6—C5—C4119.5 (6)C13—C14—H14117.9
C6—C5—H5120.2C1—N1—H1120.0
C4—C5—H5120.2C1—N1—H2120.0
C5—C6—C1121.2 (7)H1—N1—H2120.0
C5—C6—H6119.4C7—N2—S1118.3 (5)
C1—C6—H6119.4C7—N3—C9115.6 (7)
N2—C7—N3121.0 (7)C7—N3—H7122.2
N2—C7—S2130.7 (6)C9—N3—H7122.2
N3—C7—S2108.3 (6)C10—N4—C14115.7 (9)
C9—C8—S2111.3 (7)O1—S1—O2116.7 (3)
C9—C8—H8124.3O1—S1—N2105.2 (3)
S2—C8—H8124.3O2—S1—N2111.3 (3)
C8—C9—N3113.6 (7)O1—S1—C4109.1 (3)
C8—C9—H9123.2O2—S1—C4107.4 (3)
N3—C9—H9123.2N2—S1—C4106.8 (3)
N4—C10—C11125.3 (10)C8—S2—C791.1 (4)
N4—C10—H10116 (4)
N1—C1—C2—C3178.5 (7)N2—C7—N3—C9178.7 (7)
C6—C1—C2—C30.4 (11)S2—C7—N3—C90.1 (8)
C1—C2—C3—C40.4 (10)C8—C9—N3—C70.0 (11)
C2—C3—C4—C51.1 (9)C11—C10—N4—C140.1 (16)
C2—C3—C4—S1179.4 (5)C13—C14—N4—C100.0 (18)
C3—C4—C5—C62.0 (10)C7—N2—S1—O1177.1 (6)
S1—C4—C5—C6179.8 (5)C7—N2—S1—O249.8 (6)
C4—C5—C6—C12.0 (10)C7—N2—S1—C467.2 (6)
N1—C1—C6—C5179.4 (7)C3—C4—S1—O1127.4 (6)
C2—C1—C6—C51.3 (11)C5—C4—S1—O154.4 (6)
S2—C8—C9—N30.2 (11)C3—C4—S1—O20.1 (6)
N4—C10—C11—C121.3 (18)C5—C4—S1—O2178.3 (5)
C10—C11—C12—C132 (2)C3—C4—S1—N2119.5 (5)
C11—C12—C13—C142 (2)C5—C4—S1—N258.8 (6)
C12—C13—C14—N41 (2)C9—C8—S2—C70.2 (8)
N3—C7—N2—S1178.5 (5)N2—C7—S2—C8178.5 (8)
S2—C7—N2—S10.0 (10)N3—C7—S2—C80.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H7···N40.861.932.773 (9)165
N1—H1···O1i0.862.122.976 (9)176
N1—H2···O2ii0.862.493.040 (8)123
Symmetry codes: (i) x+1, y, z; (ii) y+1, x+2, z1/4.
 

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