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The asymmetric unit of the title compound, C9H9N3O2S2·C5H5N, contains a sulfathia­zole and a pyridine mol­ecule linked via N—H...N hydrogen bonds, as in the tetra­gonal polymorph. The monoclinic polymorph is unstable in air at ambient conditions and loses pyridine giving sulfathia­zole. The monoclinic polymorph belongs to the class of disappearing polymorphs; it was the first polymorph to be obtained, but could not be obtained again, after the tetra­gonal polymorph was crystallized.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020071/bt2091sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020071/bt2091Isup2.hkl
Contains datablock I

CCDC reference: 613586

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.105
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.00 Deg. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5723 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.00 Deg.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 24.00 From the CIF: _diffrn_reflns_theta_full 24.00 From the CIF: _reflns_number_total 2335 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2490 Completeness (_total/calc) 93.78% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C13 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C5 H5 N
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 7 ALERT type 3 Indicator that the structure quality may be low 2 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·C5H5NF(000) = 696
Mr = 334.43Dx = 1.402 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 38 reflections
a = 8.385 (3) Åθ = 8.0–12.3°
b = 9.272 (2) ŵ = 0.35 mm1
c = 20.704 (8) ÅT = 295 K
β = 100.10 (3)°Prism, colourless
V = 1584.7 (9) Å30.46 × 0.19 × 0.10 mm
Z = 4
Data collection top
Stoe Stadi-4 four-circle D094
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 24.0°, θmin = 2.0°
Planar graphite monochromatorh = 96
Scan width (ω) = 1.40 – 1.56, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)k = 010
2335 measured reflectionsl = 023
2335 independent reflections3 standard reflections every 60 min
1764 reflections with I > 2σ(I) intensity decay: 50.3%
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.7805P]
where P = (Fo2 + 2Fc2)/3
2335 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.26 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
S10.21912 (10)0.33196 (8)0.13187 (4)0.0413 (2)
S20.01938 (11)0.30499 (10)0.01758 (4)0.0538 (3)
O10.3541 (3)0.3350 (2)0.18558 (10)0.0543 (6)
O20.1782 (3)0.4673 (2)0.09846 (11)0.0528 (6)
C40.0481 (4)0.2765 (3)0.16403 (14)0.0364 (7)
N30.1861 (4)0.0764 (3)0.01254 (13)0.0455 (7)
C30.1030 (4)0.3391 (3)0.14276 (14)0.0413 (8)
H40.11420.41000.11050.050*
C50.0625 (4)0.1695 (3)0.21178 (14)0.0460 (8)
H50.16230.12570.22600.055*
C70.1675 (4)0.1915 (3)0.02466 (14)0.0409 (8)
N20.2572 (3)0.2057 (3)0.08398 (12)0.0442 (7)
N40.4094 (4)0.1326 (3)0.04670 (14)0.0568 (8)
C60.0705 (4)0.1280 (3)0.23813 (16)0.0516 (9)
H60.05930.05620.27000.062*
C20.2360 (4)0.2973 (3)0.16898 (15)0.0455 (8)
H30.33620.33980.15400.055*
C80.0853 (4)0.0737 (4)0.07294 (16)0.0545 (9)
H80.08600.00030.10320.065*
C140.4476 (5)0.2605 (4)0.0257 (2)0.0733 (12)
H140.39820.29040.01590.088*
C10.2216 (4)0.1918 (3)0.21776 (16)0.0477 (8)
C90.0125 (5)0.1866 (4)0.08355 (16)0.0581 (10)
H90.08860.20070.12150.070*
N10.3532 (5)0.1521 (4)0.2451 (2)0.0758 (11)
C110.5922 (5)0.1806 (4)0.14601 (17)0.0648 (11)
H110.63980.14990.18770.078*
C100.4824 (5)0.0944 (4)0.10624 (18)0.0646 (11)
H100.45820.00460.12200.078*
C130.5572 (6)0.3514 (4)0.0626 (2)0.0908 (15)
H130.58130.44030.04590.109*
C120.6293 (5)0.3108 (4)0.1232 (2)0.0722 (11)
H120.70320.37120.14890.087*
H70.254 (4)0.008 (3)0.0020 (15)0.048 (10)*
H20.337 (5)0.091 (5)0.275 (2)0.089 (16)*
H10.438 (5)0.197 (4)0.2337 (18)0.062 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0361 (5)0.0433 (4)0.0433 (4)0.0048 (4)0.0034 (4)0.0039 (4)
S20.0533 (7)0.0590 (6)0.0463 (5)0.0145 (4)0.0009 (4)0.0056 (4)
O10.0370 (14)0.0715 (16)0.0501 (13)0.0027 (12)0.0042 (11)0.0121 (12)
O20.0538 (16)0.0389 (12)0.0663 (15)0.0039 (11)0.0125 (12)0.0056 (11)
C40.035 (2)0.0362 (16)0.0359 (15)0.0051 (14)0.0006 (14)0.0045 (13)
N30.049 (2)0.0477 (17)0.0399 (15)0.0057 (15)0.0071 (14)0.0019 (13)
C30.043 (2)0.0393 (17)0.0408 (16)0.0082 (15)0.0050 (15)0.0073 (14)
C50.043 (2)0.0492 (19)0.0427 (17)0.0129 (16)0.0018 (16)0.0035 (16)
C70.040 (2)0.0438 (18)0.0403 (17)0.0021 (15)0.0109 (15)0.0031 (14)
N20.0440 (18)0.0495 (16)0.0385 (14)0.0141 (13)0.0054 (13)0.0038 (12)
N40.053 (2)0.0595 (19)0.0570 (18)0.0114 (15)0.0063 (16)0.0024 (15)
C60.055 (3)0.054 (2)0.0447 (18)0.0085 (17)0.0057 (18)0.0163 (16)
C20.039 (2)0.0460 (18)0.0516 (19)0.0130 (15)0.0081 (17)0.0065 (16)
C80.059 (3)0.064 (2)0.0405 (19)0.005 (2)0.0080 (18)0.0056 (17)
C140.072 (3)0.069 (3)0.070 (3)0.008 (2)0.015 (2)0.023 (2)
C10.047 (2)0.0476 (19)0.0500 (18)0.0052 (17)0.0132 (17)0.0007 (15)
C90.054 (3)0.078 (3)0.0385 (18)0.001 (2)0.0019 (17)0.0030 (18)
N10.060 (3)0.081 (3)0.094 (3)0.019 (2)0.034 (2)0.034 (2)
C110.083 (3)0.065 (2)0.045 (2)0.013 (2)0.006 (2)0.0025 (18)
C100.075 (3)0.060 (2)0.059 (2)0.018 (2)0.014 (2)0.0072 (19)
C130.101 (4)0.053 (2)0.103 (4)0.024 (2)0.024 (3)0.026 (2)
C120.079 (3)0.057 (2)0.073 (3)0.012 (2)0.006 (2)0.009 (2)
Geometric parameters (Å, º) top
S1—O11.441 (2)C6—H60.9300
S1—O21.445 (2)C2—C11.396 (4)
S1—N21.602 (2)C2—H30.9300
S1—C41.761 (3)C8—C91.325 (5)
S2—C91.736 (4)C8—H80.9300
S2—C71.742 (3)C14—C131.376 (6)
C4—C51.391 (4)C14—H140.9300
C4—C31.393 (4)C1—N11.376 (5)
N3—C71.342 (4)C9—H90.9300
N3—C81.382 (4)N1—H20.84 (4)
N3—H70.87 (3)N1—H10.82 (4)
C3—C21.379 (4)C11—C121.352 (5)
C3—H40.9300C11—C101.378 (5)
C5—C61.380 (4)C11—H110.9300
C5—H50.9300C10—H100.9300
C7—N21.330 (4)C13—C121.347 (5)
N4—C141.321 (4)C13—H130.9300
N4—C101.325 (5)C12—H120.9300
C6—C11.395 (5)
O1—S1—O2116.15 (15)C1—C2—H3119.7
O1—S1—N2106.08 (14)C9—C8—N3113.5 (3)
O2—S1—N2113.24 (13)C9—C8—H8123.3
O1—S1—C4107.18 (14)N3—C8—H8123.3
O2—S1—C4107.11 (14)N4—C14—C13123.0 (4)
N2—S1—C4106.56 (14)N4—C14—H14118.5
C9—S2—C790.64 (17)C13—C14—H14118.5
C5—C4—C3118.9 (3)N1—C1—C6120.9 (3)
C5—C4—S1120.1 (2)N1—C1—C2120.7 (3)
C3—C4—S1121.0 (2)C6—C1—C2118.3 (3)
C7—N3—C8114.8 (3)C8—C9—S2111.3 (3)
C7—N3—H7121 (2)C8—C9—H9124.3
C8—N3—H7124 (2)S2—C9—H9124.3
C2—C3—C4120.8 (3)C1—N1—H2117 (3)
C2—C3—H4119.6C1—N1—H1117 (3)
C4—C3—H4119.6H2—N1—H1125 (4)
C6—C5—C4120.3 (3)C12—C11—C10118.7 (4)
C6—C5—H5119.8C12—C11—H11120.7
C4—C5—H5119.8C10—C11—H11120.7
N2—C7—N3120.3 (3)N4—C10—C11123.5 (3)
N2—C7—S2130.0 (2)N4—C10—H10118.2
N3—C7—S2109.7 (2)C11—C10—H10118.2
C7—N2—S1120.1 (2)C12—C13—C14119.5 (4)
C14—N4—C10116.5 (3)C12—C13—H13120.2
C5—C6—C1121.1 (3)C14—C13—H13120.2
C5—C6—H6119.4C13—C12—C11118.8 (4)
C1—C6—H6119.4C13—C12—H12120.6
C3—C2—C1120.5 (3)C11—C12—H12120.6
C3—C2—H3119.7
O1—S1—C4—C539.1 (3)O2—S1—N2—C740.7 (3)
O2—S1—C4—C5164.4 (2)C4—S1—N2—C776.8 (3)
N2—S1—C4—C574.2 (3)C4—C5—C6—C10.1 (5)
O1—S1—C4—C3140.4 (2)C4—C3—C2—C10.4 (5)
O2—S1—C4—C315.1 (3)C7—N3—C8—C90.2 (4)
N2—S1—C4—C3106.3 (3)C10—N4—C14—C130.1 (6)
C5—C4—C3—C20.8 (4)C5—C6—C1—N1178.7 (3)
S1—C4—C3—C2178.7 (2)C5—C6—C1—C21.2 (5)
C3—C4—C5—C60.9 (5)C3—C2—C1—N1178.5 (3)
S1—C4—C5—C6178.6 (2)C3—C2—C1—C61.4 (5)
C8—N3—C7—N2179.6 (3)N3—C8—C9—S20.8 (4)
C8—N3—C7—S21.0 (3)C7—S2—C9—C81.1 (3)
C9—S2—C7—N2179.5 (3)C14—N4—C10—C110.5 (6)
C9—S2—C7—N31.2 (2)C12—C11—C10—N40.6 (6)
N3—C7—N2—S1172.0 (2)N4—C14—C13—C120.5 (8)
S2—C7—N2—S18.8 (4)C14—C13—C12—C110.3 (7)
O1—S1—N2—C7169.2 (2)C10—C11—C12—C130.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H7···N40.87 (3)1.96 (3)2.821 (4)172 (3)
N1—H1···O1i0.82 (4)2.25 (4)3.059 (5)168 (3)
N1—H2···O1ii0.84 (4)2.52 (4)3.273 (5)150 (4)
Symmetry codes: (i) x1, y, z; (ii) x, y1/2, z+1/2.
 

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