The asymmetric unit of the title compound, C
9H
9N
3O
2S
2·C
5H
5N, 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
CCDC reference: 613586
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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 | F(000) = 696 |
Mr = 334.43 | Dx = 1.402 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 38 reflections |
a = 8.385 (3) Å | θ = 8.0–12.3° |
b = 9.272 (2) Å | µ = 0.35 mm−1 |
c = 20.704 (8) Å | T = 295 K |
β = 100.10 (3)° | Prism, colourless |
V = 1584.7 (9) Å3 | 0.46 × 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 tube | θmax = 24.0°, θmin = 2.0° |
Planar graphite monochromator | h = −9→6 |
Scan width (ω) = 1.40 – 1.56, scan ratio 2θ:ω = 1.00
I(Net) and sigma(I) calculated according to Blessing (1987) | k = 0→10 |
2335 measured reflections | l = 0→23 |
2335 independent reflections | 3 standard reflections every 60 min |
1764 reflections with I > 2σ(I) | intensity decay: 50.3% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H 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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | |
S1 | 0.21912 (10) | 0.33196 (8) | 0.13187 (4) | 0.0413 (2) | |
S2 | 0.01938 (11) | 0.30499 (10) | −0.01758 (4) | 0.0538 (3) | |
O1 | 0.3541 (3) | 0.3350 (2) | 0.18558 (10) | 0.0543 (6) | |
O2 | 0.1782 (3) | 0.4673 (2) | 0.09846 (11) | 0.0528 (6) | |
C4 | 0.0481 (4) | 0.2765 (3) | 0.16403 (14) | 0.0364 (7) | |
N3 | 0.1861 (4) | 0.0764 (3) | −0.01254 (13) | 0.0455 (7) | |
C3 | −0.1030 (4) | 0.3391 (3) | 0.14276 (14) | 0.0413 (8) | |
H4 | −0.1142 | 0.4100 | 0.1105 | 0.050* | |
C5 | 0.0625 (4) | 0.1695 (3) | 0.21178 (14) | 0.0460 (8) | |
H5 | 0.1623 | 0.1257 | 0.2260 | 0.055* | |
C7 | 0.1675 (4) | 0.1915 (3) | 0.02466 (14) | 0.0409 (8) | |
N2 | 0.2572 (3) | 0.2057 (3) | 0.08398 (12) | 0.0442 (7) | |
N4 | 0.4094 (4) | −0.1326 (3) | 0.04670 (14) | 0.0568 (8) | |
C6 | −0.0705 (4) | 0.1280 (3) | 0.23813 (16) | 0.0516 (9) | |
H6 | −0.0593 | 0.0562 | 0.2700 | 0.062* | |
C2 | −0.2360 (4) | 0.2973 (3) | 0.16898 (15) | 0.0455 (8) | |
H3 | −0.3362 | 0.3398 | 0.1540 | 0.055* | |
C8 | 0.0853 (4) | 0.0737 (4) | −0.07294 (16) | 0.0545 (9) | |
H8 | 0.0860 | −0.0003 | −0.1032 | 0.065* | |
C14 | 0.4476 (5) | −0.2605 (4) | 0.0257 (2) | 0.0733 (12) | |
H14 | 0.3982 | −0.2904 | −0.0159 | 0.088* | |
C1 | −0.2216 (4) | 0.1918 (3) | 0.21776 (16) | 0.0477 (8) | |
C9 | −0.0125 (5) | 0.1866 (4) | −0.08355 (16) | 0.0581 (10) | |
H9 | −0.0886 | 0.2007 | −0.1215 | 0.070* | |
N1 | −0.3532 (5) | 0.1521 (4) | 0.2451 (2) | 0.0758 (11) | |
C11 | 0.5922 (5) | −0.1806 (4) | 0.14601 (17) | 0.0648 (11) | |
H11 | 0.6398 | −0.1499 | 0.1877 | 0.078* | |
C10 | 0.4824 (5) | −0.0944 (4) | 0.10624 (18) | 0.0646 (11) | |
H10 | 0.4582 | −0.0046 | 0.1220 | 0.078* | |
C13 | 0.5572 (6) | −0.3514 (4) | 0.0626 (2) | 0.0908 (15) | |
H13 | 0.5813 | −0.4403 | 0.0459 | 0.109* | |
C12 | 0.6293 (5) | −0.3108 (4) | 0.1232 (2) | 0.0722 (11) | |
H12 | 0.7032 | −0.3712 | 0.1489 | 0.087* | |
H7 | 0.254 (4) | 0.008 (3) | 0.0020 (15) | 0.048 (10)* | |
H2 | −0.337 (5) | 0.091 (5) | 0.275 (2) | 0.089 (16)* | |
H1 | −0.438 (5) | 0.197 (4) | 0.2337 (18) | 0.062 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0361 (5) | 0.0433 (4) | 0.0433 (4) | 0.0048 (4) | 0.0034 (4) | −0.0039 (4) |
S2 | 0.0533 (7) | 0.0590 (6) | 0.0463 (5) | 0.0145 (4) | 0.0009 (4) | 0.0056 (4) |
O1 | 0.0370 (14) | 0.0715 (16) | 0.0501 (13) | 0.0027 (12) | −0.0042 (11) | −0.0121 (12) |
O2 | 0.0538 (16) | 0.0389 (12) | 0.0663 (15) | 0.0039 (11) | 0.0125 (12) | 0.0056 (11) |
C4 | 0.035 (2) | 0.0362 (16) | 0.0359 (15) | 0.0051 (14) | 0.0006 (14) | −0.0045 (13) |
N3 | 0.049 (2) | 0.0477 (17) | 0.0399 (15) | 0.0057 (15) | 0.0071 (14) | −0.0019 (13) |
C3 | 0.043 (2) | 0.0393 (17) | 0.0408 (16) | 0.0082 (15) | 0.0050 (15) | 0.0073 (14) |
C5 | 0.043 (2) | 0.0492 (19) | 0.0427 (17) | 0.0129 (16) | −0.0018 (16) | 0.0035 (16) |
C7 | 0.040 (2) | 0.0438 (18) | 0.0403 (17) | 0.0021 (15) | 0.0109 (15) | 0.0031 (14) |
N2 | 0.0440 (18) | 0.0495 (16) | 0.0385 (14) | 0.0141 (13) | 0.0054 (13) | −0.0038 (12) |
N4 | 0.053 (2) | 0.0595 (19) | 0.0570 (18) | 0.0114 (15) | 0.0063 (16) | −0.0024 (15) |
C6 | 0.055 (3) | 0.054 (2) | 0.0447 (18) | 0.0085 (17) | 0.0057 (18) | 0.0163 (16) |
C2 | 0.039 (2) | 0.0460 (18) | 0.0516 (19) | 0.0130 (15) | 0.0081 (17) | 0.0065 (16) |
C8 | 0.059 (3) | 0.064 (2) | 0.0405 (19) | −0.005 (2) | 0.0080 (18) | −0.0056 (17) |
C14 | 0.072 (3) | 0.069 (3) | 0.070 (3) | 0.008 (2) | −0.015 (2) | −0.023 (2) |
C1 | 0.047 (2) | 0.0476 (19) | 0.0500 (18) | 0.0052 (17) | 0.0132 (17) | 0.0007 (15) |
C9 | 0.054 (3) | 0.078 (3) | 0.0385 (18) | −0.001 (2) | −0.0019 (17) | 0.0030 (18) |
N1 | 0.060 (3) | 0.081 (3) | 0.094 (3) | 0.019 (2) | 0.034 (2) | 0.034 (2) |
C11 | 0.083 (3) | 0.065 (2) | 0.045 (2) | 0.013 (2) | 0.006 (2) | 0.0025 (18) |
C10 | 0.075 (3) | 0.060 (2) | 0.059 (2) | 0.018 (2) | 0.014 (2) | −0.0072 (19) |
C13 | 0.101 (4) | 0.053 (2) | 0.103 (4) | 0.024 (2) | −0.024 (3) | −0.026 (2) |
C12 | 0.079 (3) | 0.057 (2) | 0.073 (3) | 0.012 (2) | −0.006 (2) | 0.009 (2) |
Geometric parameters (Å, º) top
S1—O1 | 1.441 (2) | C6—H6 | 0.9300 |
S1—O2 | 1.445 (2) | C2—C1 | 1.396 (4) |
S1—N2 | 1.602 (2) | C2—H3 | 0.9300 |
S1—C4 | 1.761 (3) | C8—C9 | 1.325 (5) |
S2—C9 | 1.736 (4) | C8—H8 | 0.9300 |
S2—C7 | 1.742 (3) | C14—C13 | 1.376 (6) |
C4—C5 | 1.391 (4) | C14—H14 | 0.9300 |
C4—C3 | 1.393 (4) | C1—N1 | 1.376 (5) |
N3—C7 | 1.342 (4) | C9—H9 | 0.9300 |
N3—C8 | 1.382 (4) | N1—H2 | 0.84 (4) |
N3—H7 | 0.87 (3) | N1—H1 | 0.82 (4) |
C3—C2 | 1.379 (4) | C11—C12 | 1.352 (5) |
C3—H4 | 0.9300 | C11—C10 | 1.378 (5) |
C5—C6 | 1.380 (4) | C11—H11 | 0.9300 |
C5—H5 | 0.9300 | C10—H10 | 0.9300 |
C7—N2 | 1.330 (4) | C13—C12 | 1.347 (5) |
N4—C14 | 1.321 (4) | C13—H13 | 0.9300 |
N4—C10 | 1.325 (5) | C12—H12 | 0.9300 |
C6—C1 | 1.395 (5) | | |
| | | |
O1—S1—O2 | 116.15 (15) | C1—C2—H3 | 119.7 |
O1—S1—N2 | 106.08 (14) | C9—C8—N3 | 113.5 (3) |
O2—S1—N2 | 113.24 (13) | C9—C8—H8 | 123.3 |
O1—S1—C4 | 107.18 (14) | N3—C8—H8 | 123.3 |
O2—S1—C4 | 107.11 (14) | N4—C14—C13 | 123.0 (4) |
N2—S1—C4 | 106.56 (14) | N4—C14—H14 | 118.5 |
C9—S2—C7 | 90.64 (17) | C13—C14—H14 | 118.5 |
C5—C4—C3 | 118.9 (3) | N1—C1—C6 | 120.9 (3) |
C5—C4—S1 | 120.1 (2) | N1—C1—C2 | 120.7 (3) |
C3—C4—S1 | 121.0 (2) | C6—C1—C2 | 118.3 (3) |
C7—N3—C8 | 114.8 (3) | C8—C9—S2 | 111.3 (3) |
C7—N3—H7 | 121 (2) | C8—C9—H9 | 124.3 |
C8—N3—H7 | 124 (2) | S2—C9—H9 | 124.3 |
C2—C3—C4 | 120.8 (3) | C1—N1—H2 | 117 (3) |
C2—C3—H4 | 119.6 | C1—N1—H1 | 117 (3) |
C4—C3—H4 | 119.6 | H2—N1—H1 | 125 (4) |
C6—C5—C4 | 120.3 (3) | C12—C11—C10 | 118.7 (4) |
C6—C5—H5 | 119.8 | C12—C11—H11 | 120.7 |
C4—C5—H5 | 119.8 | C10—C11—H11 | 120.7 |
N2—C7—N3 | 120.3 (3) | N4—C10—C11 | 123.5 (3) |
N2—C7—S2 | 130.0 (2) | N4—C10—H10 | 118.2 |
N3—C7—S2 | 109.7 (2) | C11—C10—H10 | 118.2 |
C7—N2—S1 | 120.1 (2) | C12—C13—C14 | 119.5 (4) |
C14—N4—C10 | 116.5 (3) | C12—C13—H13 | 120.2 |
C5—C6—C1 | 121.1 (3) | C14—C13—H13 | 120.2 |
C5—C6—H6 | 119.4 | C13—C12—C11 | 118.8 (4) |
C1—C6—H6 | 119.4 | C13—C12—H12 | 120.6 |
C3—C2—C1 | 120.5 (3) | C11—C12—H12 | 120.6 |
C3—C2—H3 | 119.7 | | |
| | | |
O1—S1—C4—C5 | −39.1 (3) | O2—S1—N2—C7 | −40.7 (3) |
O2—S1—C4—C5 | −164.4 (2) | C4—S1—N2—C7 | 76.8 (3) |
N2—S1—C4—C5 | 74.2 (3) | C4—C5—C6—C1 | −0.1 (5) |
O1—S1—C4—C3 | 140.4 (2) | C4—C3—C2—C1 | 0.4 (5) |
O2—S1—C4—C3 | 15.1 (3) | C7—N3—C8—C9 | 0.2 (4) |
N2—S1—C4—C3 | −106.3 (3) | C10—N4—C14—C13 | −0.1 (6) |
C5—C4—C3—C2 | 0.8 (4) | C5—C6—C1—N1 | −178.7 (3) |
S1—C4—C3—C2 | −178.7 (2) | C5—C6—C1—C2 | 1.2 (5) |
C3—C4—C5—C6 | −0.9 (5) | C3—C2—C1—N1 | 178.5 (3) |
S1—C4—C5—C6 | 178.6 (2) | C3—C2—C1—C6 | −1.4 (5) |
C8—N3—C7—N2 | 179.6 (3) | N3—C8—C9—S2 | 0.8 (4) |
C8—N3—C7—S2 | −1.0 (3) | C7—S2—C9—C8 | −1.1 (3) |
C9—S2—C7—N2 | −179.5 (3) | C14—N4—C10—C11 | −0.5 (6) |
C9—S2—C7—N3 | 1.2 (2) | C12—C11—C10—N4 | 0.6 (6) |
N3—C7—N2—S1 | −172.0 (2) | N4—C14—C13—C12 | 0.5 (8) |
S2—C7—N2—S1 | 8.8 (4) | C14—C13—C12—C11 | −0.3 (7) |
O1—S1—N2—C7 | −169.2 (2) | C10—C11—C12—C13 | −0.2 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H7···N4 | 0.87 (3) | 1.96 (3) | 2.821 (4) | 172 (3) |
N1—H1···O1i | 0.82 (4) | 2.25 (4) | 3.059 (5) | 168 (3) |
N1—H2···O1ii | 0.84 (4) | 2.52 (4) | 3.273 (5) | 150 (4) |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2. |