The title compound, C
5H
4ClNO
3S, was obtained by hydrolysis of 4-chloropyridine-3-sulfonamide in dilute hydrochloric acid. In the crystal structure, one-dimensional chains are formed
via N—H
O hydrogen bonds. In addition, weak C—H
Cl hydrogen bonds link these chains into a two-dimensional network
Supporting information
CCDC reference: 605122
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.133
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. O3 .. 2.98 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C1 .. 3.01 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT; 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: PLATON (Spek, 2003).
4-chloropyridine-3-sulfonic acid
top
Crystal data top
C5H4ClNO3S | F(000) = 392 |
Mr = 193.60 | Dx = 1.933 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2647 reflections |
a = 7.1433 (7) Å | θ = 6.0–56.5° |
b = 6.8424 (7) Å | µ = 0.83 mm−1 |
c = 13.7397 (14) Å | T = 293 K |
β = 97.783 (2)° | Prism, colorless |
V = 665.37 (12) Å3 | 0.49 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1450 independent reflections |
Radiation source: fine-focus sealed tube | 1343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.118 |
φ and ω scans | θmax = 27.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.674, Tmax = 0.890 | k = −8→8 |
3744 measured reflections | l = −17→9 |
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)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.0236P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
1450 reflections | Δρmax = 0.68 e Å−3 |
105 parameters | Δρmin = −0.62 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.097 (8) |
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 | |
S | 0.92026 (7) | 0.17158 (8) | 0.86290 (3) | 0.0224 (3) | |
Cl | 1.32204 (7) | 0.21185 (9) | 0.77151 (4) | 0.0278 (3) | |
O1 | 1.0119 (2) | 0.3448 (2) | 0.90884 (12) | 0.0321 (4) | |
O2 | 1.0189 (2) | −0.0074 (3) | 0.89154 (11) | 0.0314 (4) | |
O3 | 0.7196 (2) | 0.1667 (3) | 0.86653 (12) | 0.0376 (5) | |
N1 | 0.7842 (3) | 0.2005 (3) | 0.57155 (14) | 0.0273 (5) | |
C1 | 0.7770 (3) | 0.1862 (3) | 0.66803 (17) | 0.0241 (5) | |
H1 | 0.6609 | 0.1699 | 0.6905 | 0.029* | |
C2 | 0.9389 (3) | 0.1955 (3) | 0.73442 (16) | 0.0202 (5) | |
C3 | 1.1100 (3) | 0.2158 (3) | 0.69699 (15) | 0.0216 (5) | |
C4 | 1.1129 (3) | 0.2373 (3) | 0.59699 (16) | 0.0286 (5) | |
H4 | 1.2263 | 0.2559 | 0.5720 | 0.034* | |
C5 | 0.9453 (4) | 0.2306 (3) | 0.53568 (17) | 0.0303 (5) | |
H5 | 0.9442 | 0.2472 | 0.4684 | 0.036* | |
H1A | 0.672 (5) | 0.182 (4) | 0.528 (3) | 0.047 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0170 (4) | 0.0385 (4) | 0.0121 (3) | 0.00259 (18) | 0.0033 (2) | −0.00091 (19) |
Cl | 0.0159 (3) | 0.0474 (4) | 0.0197 (4) | −0.00331 (19) | 0.0010 (2) | 0.0023 (2) |
O1 | 0.0336 (10) | 0.0419 (9) | 0.0192 (8) | 0.0036 (7) | −0.0023 (6) | −0.0073 (7) |
O2 | 0.0341 (9) | 0.0411 (9) | 0.0204 (8) | 0.0068 (7) | 0.0086 (6) | 0.0069 (7) |
O3 | 0.0186 (8) | 0.0730 (12) | 0.0225 (8) | 0.0026 (7) | 0.0079 (6) | −0.0013 (8) |
N1 | 0.0233 (10) | 0.0389 (10) | 0.0176 (10) | 0.0020 (7) | −0.0048 (7) | −0.0018 (7) |
C1 | 0.0154 (10) | 0.0378 (11) | 0.0194 (11) | 0.0022 (8) | 0.0027 (8) | −0.0017 (8) |
C2 | 0.0207 (11) | 0.0260 (10) | 0.0141 (10) | 0.0016 (7) | 0.0025 (8) | −0.0005 (7) |
C3 | 0.0204 (10) | 0.0274 (10) | 0.0173 (11) | −0.0034 (7) | 0.0028 (8) | −0.0001 (8) |
C4 | 0.0242 (12) | 0.0453 (13) | 0.0174 (11) | −0.0054 (9) | 0.0066 (9) | 0.0010 (10) |
C5 | 0.0360 (14) | 0.0436 (13) | 0.0114 (10) | −0.0026 (10) | 0.0031 (9) | 0.0005 (9) |
Geometric parameters (Å, º) top
S—O2 | 1.4405 (16) | C1—C2 | 1.374 (3) |
S—O3 | 1.4411 (17) | C1—H1 | 0.9300 |
S—O1 | 1.4559 (17) | C2—C3 | 1.396 (3) |
S—C2 | 1.796 (2) | C3—C4 | 1.385 (3) |
Cl—C3 | 1.710 (2) | C4—C5 | 1.368 (3) |
N1—C5 | 1.328 (3) | C4—H4 | 0.9300 |
N1—C1 | 1.337 (3) | C5—H5 | 0.9300 |
N1—H1A | 0.94 (3) | | |
| | | |
O2—S—O3 | 115.01 (10) | C1—C2—C3 | 117.4 (2) |
O2—S—O1 | 113.50 (10) | C1—C2—S | 118.72 (17) |
O3—S—O1 | 113.25 (11) | C3—C2—S | 123.81 (16) |
O2—S—C2 | 104.32 (9) | C4—C3—C2 | 120.50 (19) |
O3—S—C2 | 104.04 (10) | C4—C3—Cl | 117.71 (18) |
O1—S—C2 | 105.27 (10) | C2—C3—Cl | 121.78 (17) |
C5—N1—C1 | 122.1 (2) | C5—C4—C3 | 118.6 (2) |
C5—N1—H1A | 120 (2) | C5—C4—H4 | 120.7 |
C1—N1—H1A | 118 (2) | C3—C4—H4 | 120.7 |
N1—C1—C2 | 120.8 (2) | N1—C5—C4 | 120.4 (2) |
N1—C1—H1 | 119.6 | N1—C5—H5 | 119.8 |
C2—C1—H1 | 119.6 | C4—C5—H5 | 119.8 |
| | | |
C5—N1—C1—C2 | −2.3 (3) | C1—C2—C3—C4 | 3.7 (3) |
N1—C1—C2—C3 | −1.4 (3) | S—C2—C3—C4 | −178.74 (16) |
N1—C1—C2—S | −179.05 (16) | C1—C2—C3—Cl | −175.36 (15) |
O2—S—C2—C1 | 115.07 (16) | S—C2—C3—Cl | 2.2 (3) |
O3—S—C2—C1 | −5.83 (19) | C2—C3—C4—C5 | −2.5 (3) |
O1—S—C2—C1 | −125.18 (16) | Cl—C3—C4—C5 | 176.63 (18) |
O2—S—C2—C3 | −62.45 (19) | C1—N1—C5—C4 | 3.6 (4) |
O3—S—C2—C3 | 176.65 (17) | C3—C4—C5—N1 | −1.2 (3) |
O1—S—C2—C3 | 57.30 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cli | 0.93 | 2.74 | 3.639 (2) | 162 |
N1—H1A···O1i | 0.94 (3) | 1.88 (4) | 2.775 (2) | 159 (3) |
N1—H1A···Si | 0.94 (3) | 2.88 (3) | 3.705 (2) | 147 (2) |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |