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The title tetragonal polymorph is one of the two sulfathiazole–pyridine adducts, C
9H
9N
3O
2S
2·C
5H
5N, 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 N
aniline—H
O
sulfonyl form a three-dimensional network. Pyridine molecules linked to sulfathiazole molecules by N
amino—H
N
pyridine hydrogen bonds are located in the channels of the sulfathiazole framework which extend along the 4
1 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. B
28, 272–283].
Supporting information
CCDC reference: 613647
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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·C5H5N | Dx = 1.412 Mg m−3 |
Mr = 334.43 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 69 reflections |
Hall symbol: P 4w | θ = 10.1–14.6° |
a = 8.670 (2) Å | µ = 0.35 mm−1 |
c = 20.927 (10) Å | T = 295 K |
V = 1573.2 (9) Å3 | Pyramid, colourless |
Z = 4 | 0.46 × 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 tube | Rint = 0.021 |
Planar graphite monochromator | θmax = 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 = −7→7 |
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997) | k = −9→10 |
Tmin = 0.771, Tmax = 0.874 | l = −22→25 |
2518 measured reflections | 3 standard reflections every 180 min |
2518 independent reflections | intensity decay: 38.0% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H 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 reflections | Δρmax = 0.23 e Å−3 |
205 parameters | Δρmin = −0.28 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 1006 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 1.3987 (8) | 0.9982 (8) | 1.0027 (3) | 0.0443 (18) | |
C2 | 1.3779 (8) | 0.9368 (8) | 1.0632 (4) | 0.0482 (18) | |
H3 | 1.4626 | 0.9230 | 1.0899 | 0.058* | |
C3 | 1.2334 (8) | 0.8962 (7) | 1.0842 (3) | 0.0399 (18) | |
H4 | 1.2213 | 0.8545 | 1.1249 | 0.048* | |
C4 | 1.1060 (7) | 0.9164 (7) | 1.0457 (3) | 0.0354 (16) | |
C5 | 1.1249 (8) | 0.9763 (8) | 0.9843 (3) | 0.0393 (17) | |
H5 | 1.0403 | 0.9875 | 0.9574 | 0.047* | |
C6 | 1.2697 (8) | 1.0186 (8) | 0.9639 (3) | 0.0458 (19) | |
H6 | 1.2817 | 1.0615 | 0.9235 | 0.055* | |
C7 | 0.9290 (8) | 0.5987 (9) | 1.0216 (3) | 0.0441 (18) | |
C8 | 1.0724 (12) | 0.3522 (10) | 1.0288 (5) | 0.079 (3) | |
H8 | 1.1372 | 0.2693 | 1.0375 | 0.095* | |
C9 | 0.9600 (11) | 0.3493 (10) | 0.9867 (4) | 0.071 (3) | |
H9 | 0.9367 | 0.2630 | 0.9621 | 0.085* | |
C10 | 0.5010 (14) | 0.6091 (11) | 0.9410 (5) | 0.081 (3) | |
H10 | 0.545 (9) | 0.699 (10) | 0.969 (4) | 0.08 (3)* | |
C11 | 0.3512 (15) | 0.6119 (14) | 0.9260 (7) | 0.111 (4) | |
H11 | 0.2847 | 0.6835 | 0.9444 | 0.133* | |
C12 | 0.2994 (13) | 0.5063 (18) | 0.8829 (7) | 0.108 (4) | |
H12 | 0.1969 | 0.5063 | 0.8697 | 0.130* | |
C13 | 0.4001 (14) | 0.4017 (15) | 0.8596 (6) | 0.118 (4) | |
H13 | 0.3677 | 0.3255 | 0.8313 | 0.141* | |
C14 | 0.5481 (12) | 0.4100 (13) | 0.8782 (6) | 0.100 (4) | |
H14 | 0.6170 | 0.3387 | 0.8613 | 0.120* | |
N1 | 1.5415 (8) | 1.0414 (9) | 0.9827 (3) | 0.075 (2) | |
H1 | 1.6195 | 1.0307 | 1.0076 | 0.06 (3)* | |
H2 | 1.5537 | 1.0794 | 0.9451 | 0.06 (3)* | |
N2 | 0.8590 (6) | 0.7341 (6) | 1.0226 (3) | 0.0420 (14) | |
N3 | 0.8803 (8) | 0.4852 (7) | 0.9826 (3) | 0.0569 (17) | |
H7 | 0.8042 | 0.4973 | 0.9567 | 0.068* | |
N4 | 0.6015 (8) | 0.5116 (8) | 0.9186 (3) | 0.065 (2) | |
O1 | 0.8184 (5) | 0.9919 (5) | 1.0642 (3) | 0.0573 (14) | |
O2 | 0.9366 (6) | 0.8013 (5) | 1.1356 (2) | 0.0492 (13) | |
S1 | 0.9210 (2) | 0.86308 (19) | 1.07180 (10) | 0.0420 (4) | |
S2 | 1.0846 (3) | 0.5297 (2) | 1.06594 (11) | 0.0626 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.036 (4) | 0.054 (5) | 0.043 (5) | 0.003 (4) | 0.003 (4) | 0.000 (4) |
C2 | 0.045 (4) | 0.053 (4) | 0.047 (5) | 0.004 (3) | −0.013 (4) | −0.003 (4) |
C3 | 0.048 (5) | 0.037 (4) | 0.035 (4) | −0.002 (3) | −0.005 (4) | 0.005 (3) |
C4 | 0.035 (4) | 0.033 (4) | 0.038 (4) | 0.003 (3) | 0.006 (3) | −0.011 (3) |
C5 | 0.047 (4) | 0.041 (4) | 0.029 (4) | 0.004 (3) | −0.005 (4) | −0.004 (3) |
C6 | 0.039 (4) | 0.054 (5) | 0.045 (4) | 0.004 (4) | 0.003 (4) | 0.003 (4) |
C7 | 0.048 (4) | 0.047 (5) | 0.037 (4) | −0.010 (4) | 0.005 (4) | −0.004 (4) |
C8 | 0.112 (8) | 0.048 (5) | 0.077 (6) | 0.023 (5) | −0.018 (6) | −0.015 (5) |
C9 | 0.101 (7) | 0.045 (5) | 0.067 (6) | −0.003 (5) | −0.016 (6) | −0.015 (5) |
C10 | 0.104 (9) | 0.056 (7) | 0.082 (8) | −0.002 (7) | 0.000 (7) | −0.023 (6) |
C11 | 0.081 (9) | 0.102 (10) | 0.150 (12) | 0.035 (7) | 0.018 (9) | −0.010 (9) |
C12 | 0.055 (7) | 0.147 (12) | 0.124 (11) | 0.015 (8) | −0.021 (7) | 0.032 (9) |
C13 | 0.082 (9) | 0.146 (11) | 0.125 (10) | 0.009 (8) | −0.039 (7) | −0.073 (9) |
C14 | 0.070 (7) | 0.111 (9) | 0.120 (9) | 0.022 (6) | −0.003 (7) | −0.065 (8) |
N1 | 0.050 (5) | 0.124 (7) | 0.050 (5) | −0.020 (4) | 0.000 (4) | 0.008 (5) |
N2 | 0.049 (4) | 0.036 (4) | 0.041 (3) | −0.005 (3) | −0.006 (3) | −0.009 (3) |
N3 | 0.076 (5) | 0.049 (4) | 0.046 (4) | −0.011 (4) | −0.012 (4) | −0.008 (3) |
N4 | 0.069 (5) | 0.058 (5) | 0.068 (5) | 0.001 (4) | −0.008 (4) | −0.021 (4) |
O1 | 0.044 (3) | 0.050 (3) | 0.078 (4) | 0.013 (2) | −0.002 (3) | −0.008 (3) |
O2 | 0.065 (4) | 0.045 (3) | 0.038 (3) | −0.007 (3) | 0.006 (3) | 0.001 (2) |
S1 | 0.0418 (10) | 0.0385 (10) | 0.0459 (10) | −0.0012 (9) | 0.0007 (10) | −0.0049 (10) |
S2 | 0.0812 (15) | 0.0457 (11) | 0.0610 (13) | 0.0084 (10) | −0.0203 (13) | −0.0111 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.360 (9) | C9—H9 | 0.9300 |
C1—C2 | 1.386 (10) | C10—N4 | 1.302 (11) |
C1—C6 | 1.393 (9) | C10—C11 | 1.336 (15) |
C2—C3 | 1.374 (9) | C10—H10 | 1.04 (9) |
C2—H3 | 0.9300 | C11—C12 | 1.362 (15) |
C3—C4 | 1.379 (8) | C11—H11 | 0.9300 |
C3—H4 | 0.9300 | C12—C13 | 1.350 (15) |
C4—C5 | 1.395 (9) | C12—H12 | 0.9300 |
C4—S1 | 1.757 (6) | C13—C14 | 1.343 (13) |
C5—C6 | 1.376 (9) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—N4 | 1.305 (11) |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—N2 | 1.321 (8) | N1—H1 | 0.8600 |
C7—N3 | 1.346 (8) | N1—H2 | 0.8600 |
C7—S2 | 1.744 (8) | N2—S1 | 1.613 (6) |
C8—C9 | 1.314 (11) | N3—H7 | 0.8600 |
C8—S2 | 1.727 (8) | O1—S1 | 1.437 (4) |
C8—H8 | 0.9300 | O2—S1 | 1.444 (5) |
C9—N3 | 1.369 (10) | | |
| | | |
N1—C1—C2 | 120.4 (7) | C11—C10—H10 | 118 (4) |
N1—C1—C6 | 121.1 (7) | C10—C11—C12 | 117.6 (11) |
C2—C1—C6 | 118.5 (7) | C10—C11—H11 | 121.2 |
C3—C2—C1 | 120.6 (7) | C12—C11—H11 | 121.2 |
C3—C2—H3 | 119.7 | C13—C12—C11 | 118.5 (11) |
C1—C2—H3 | 119.7 | C13—C12—H12 | 120.8 |
C2—C3—C4 | 120.7 (6) | C11—C12—H12 | 120.8 |
C2—C3—H4 | 119.6 | C14—C13—C12 | 118.5 (11) |
C4—C3—H4 | 119.6 | C14—C13—H13 | 120.8 |
C3—C4—C5 | 119.5 (6) | C12—C13—H13 | 120.8 |
C3—C4—S1 | 121.0 (5) | N4—C14—C13 | 124.3 (9) |
C5—C4—S1 | 119.5 (5) | N4—C14—H14 | 117.9 |
C6—C5—C4 | 119.5 (6) | C13—C14—H14 | 117.9 |
C6—C5—H5 | 120.2 | C1—N1—H1 | 120.0 |
C4—C5—H5 | 120.2 | C1—N1—H2 | 120.0 |
C5—C6—C1 | 121.2 (7) | H1—N1—H2 | 120.0 |
C5—C6—H6 | 119.4 | C7—N2—S1 | 118.3 (5) |
C1—C6—H6 | 119.4 | C7—N3—C9 | 115.6 (7) |
N2—C7—N3 | 121.0 (7) | C7—N3—H7 | 122.2 |
N2—C7—S2 | 130.7 (6) | C9—N3—H7 | 122.2 |
N3—C7—S2 | 108.3 (6) | C10—N4—C14 | 115.7 (9) |
C9—C8—S2 | 111.3 (7) | O1—S1—O2 | 116.7 (3) |
C9—C8—H8 | 124.3 | O1—S1—N2 | 105.2 (3) |
S2—C8—H8 | 124.3 | O2—S1—N2 | 111.3 (3) |
C8—C9—N3 | 113.6 (7) | O1—S1—C4 | 109.1 (3) |
C8—C9—H9 | 123.2 | O2—S1—C4 | 107.4 (3) |
N3—C9—H9 | 123.2 | N2—S1—C4 | 106.8 (3) |
N4—C10—C11 | 125.3 (10) | C8—S2—C7 | 91.1 (4) |
N4—C10—H10 | 116 (4) | | |
| | | |
N1—C1—C2—C3 | 178.5 (7) | N2—C7—N3—C9 | −178.7 (7) |
C6—C1—C2—C3 | 0.4 (11) | S2—C7—N3—C9 | 0.1 (8) |
C1—C2—C3—C4 | −0.4 (10) | C8—C9—N3—C7 | 0.0 (11) |
C2—C3—C4—C5 | 1.1 (9) | C11—C10—N4—C14 | 0.1 (16) |
C2—C3—C4—S1 | 179.4 (5) | C13—C14—N4—C10 | 0.0 (18) |
C3—C4—C5—C6 | −2.0 (10) | C7—N2—S1—O1 | −177.1 (6) |
S1—C4—C5—C6 | 179.8 (5) | C7—N2—S1—O2 | −49.8 (6) |
C4—C5—C6—C1 | 2.0 (10) | C7—N2—S1—C4 | 67.2 (6) |
N1—C1—C6—C5 | −179.4 (7) | C3—C4—S1—O1 | 127.4 (6) |
C2—C1—C6—C5 | −1.3 (11) | C5—C4—S1—O1 | −54.4 (6) |
S2—C8—C9—N3 | −0.2 (11) | C3—C4—S1—O2 | 0.1 (6) |
N4—C10—C11—C12 | −1.3 (18) | C5—C4—S1—O2 | 178.3 (5) |
C10—C11—C12—C13 | 2 (2) | C3—C4—S1—N2 | −119.5 (5) |
C11—C12—C13—C14 | −2 (2) | C5—C4—S1—N2 | 58.8 (6) |
C12—C13—C14—N4 | 1 (2) | C9—C8—S2—C7 | 0.2 (8) |
N3—C7—N2—S1 | 178.5 (5) | N2—C7—S2—C8 | 178.5 (8) |
S2—C7—N2—S1 | 0.0 (10) | N3—C7—S2—C8 | −0.2 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H7···N4 | 0.86 | 1.93 | 2.773 (9) | 165 |
N1—H1···O1i | 0.86 | 2.12 | 2.976 (9) | 176 |
N1—H2···O2ii | 0.86 | 2.49 | 3.040 (8) | 123 |
Symmetry codes: (i) x+1, y, z; (ii) y+1, −x+2, z−1/4. |
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