organic compounds
4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
aSchool of Pharmaceutical Science & Technology, Tianjin University, Tianjin 300072, People's Republic of China, and bDepartment of Pharmaceutics, Medical College of Chinese People's Armed Police Force, Tianjin 300162, People's Republic of China
*Correspondence e-mail: zpw0803@gmail.com
In the 11H10N3O4S·C2Cl3O2, the dihedral angle between the two six-membered rings is 69.2 (1)°. The molecules are connected via intermolecular N—H⋯O hydrogen bonding.
of the title compound, CExperimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S160053680800069X/nc2087sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680800069X/nc2087Isup2.hkl
0.5 g(1.8 mmol) of 4-nitro-N-(pyridin-4-yl)benzenesulfonamide was dissolved in a mixture of trichloroacetic acid (2.0 mmol,0.33 g) and ethyl acetate (5 ml). Colorless crystals of the title compound were obtained by slow evaporation of the solvent.
The C—H H atoms were positioned with idealized geometry and were refined using a riding model. The N—H H atoms were located in difference map and were refined with varying coordinates and varying isotropic displacement parameters.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii. |
C11H10N3O4S·C2Cl3O2 | F(000) = 896 |
Mr = 442.65 | Dx = 1.703 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.017 (4) Å | Cell parameters from 4622 reflections |
b = 6.2187 (12) Å | θ = 1.8–28.1° |
c = 12.719 (3) Å | µ = 0.69 mm−1 |
β = 97.48 (3)° | T = 113 K |
V = 1726.6 (6) Å3 | Lamellar, colorless |
Z = 4 | 0.14 × 0.12 × 0.04 mm |
Rigaku Saturn diffractometer | 3017 independent reflections |
Radiation source: rotating anode | 2440 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.059 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −26→26 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −7→7 |
Tmin = 0.910, Tmax = 0.973 | l = −15→13 |
9585 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0873P)2] where P = (Fo2 + 2Fc2)/3 |
3017 reflections | (Δ/σ)max = 0.001 |
243 parameters | Δρmax = 0.57 e Å−3 |
2 restraints | Δρmin = −0.54 e Å−3 |
C11H10N3O4S·C2Cl3O2 | V = 1726.6 (6) Å3 |
Mr = 442.65 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.017 (4) Å | µ = 0.69 mm−1 |
b = 6.2187 (12) Å | T = 113 K |
c = 12.719 (3) Å | 0.14 × 0.12 × 0.04 mm |
β = 97.48 (3)° |
Rigaku Saturn diffractometer | 3017 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 2440 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.973 | Rint = 0.059 |
9585 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 2 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.57 e Å−3 |
3017 reflections | Δρmin = −0.54 e Å−3 |
243 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.18257 (4) | 1.36555 (14) | 0.07245 (7) | 0.0191 (3) | |
O1 | 0.18542 (11) | 1.5313 (4) | 0.1516 (2) | 0.0249 (6) | |
O2 | 0.16464 (11) | 1.4166 (4) | −0.03720 (19) | 0.0246 (6) | |
O3 | 0.04962 (13) | 0.5416 (5) | 0.2777 (2) | 0.0357 (7) | |
O4 | −0.00146 (13) | 0.5394 (5) | 0.1197 (2) | 0.0409 (8) | |
N1 | 0.30157 (14) | 0.6878 (5) | −0.0407 (3) | 0.0231 (7) | |
N2 | 0.25080 (13) | 1.2586 (5) | 0.0880 (2) | 0.0193 (7) | |
N3 | 0.03717 (14) | 0.6156 (5) | 0.1877 (3) | 0.0248 (7) | |
C1 | 0.26602 (16) | 1.0661 (5) | 0.0425 (3) | 0.0182 (8) | |
C2 | 0.31203 (16) | 0.9400 (6) | 0.0978 (3) | 0.0219 (8) | |
H2A | 0.3310 | 0.9837 | 0.1639 | 0.026* | |
C3 | 0.32893 (16) | 0.7525 (6) | 0.0544 (3) | 0.0241 (8) | |
H3 | 0.3597 | 0.6688 | 0.0910 | 0.029* | |
C4 | 0.25743 (16) | 0.8040 (6) | −0.0958 (3) | 0.0225 (8) | |
H4 | 0.2395 | 0.7554 | −0.1618 | 0.027* | |
C5 | 0.23811 (16) | 0.9937 (6) | −0.0568 (3) | 0.0209 (8) | |
H5 | 0.2071 | 1.0732 | −0.0954 | 0.025* | |
C6 | 0.13549 (15) | 1.1534 (5) | 0.1065 (3) | 0.0185 (8) | |
C7 | 0.09757 (15) | 1.0470 (6) | 0.0274 (3) | 0.0213 (8) | |
H7 | 0.0944 | 1.0934 | −0.0426 | 0.026* | |
C8 | 0.06426 (16) | 0.8695 (6) | 0.0547 (3) | 0.0216 (8) | |
H8 | 0.0387 | 0.7945 | 0.0034 | 0.026* | |
C9 | 0.07022 (15) | 0.8085 (6) | 0.1592 (3) | 0.0209 (8) | |
C10 | 0.10690 (16) | 0.9146 (6) | 0.2399 (3) | 0.0219 (8) | |
H10 | 0.1088 | 0.8706 | 0.3101 | 0.026* | |
C11 | 0.14059 (16) | 1.0888 (6) | 0.2117 (3) | 0.0232 (8) | |
H11 | 0.1665 | 1.1622 | 0.2632 | 0.028* | |
Cl1 | 0.43685 (4) | 0.58693 (15) | 0.39003 (8) | 0.0283 (3) | |
Cl2 | 0.46462 (5) | 0.17077 (17) | 0.30622 (9) | 0.0365 (3) | |
Cl3 | 0.41727 (4) | 0.20184 (16) | 0.50681 (7) | 0.0291 (3) | |
O5 | 0.31493 (11) | 0.1505 (4) | 0.33912 (19) | 0.0230 (6) | |
O6 | 0.33887 (11) | 0.4175 (4) | 0.2360 (2) | 0.0265 (6) | |
C12 | 0.41404 (16) | 0.3150 (6) | 0.3785 (3) | 0.0212 (8) | |
C13 | 0.34910 (16) | 0.2939 (5) | 0.3118 (3) | 0.0180 (7) | |
H1 | 0.3107 (17) | 0.568 (4) | −0.075 (3) | 0.028 (11)* | |
H2 | 0.2756 (17) | 1.324 (6) | 0.140 (3) | 0.047 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0240 (5) | 0.0171 (5) | 0.0161 (5) | 0.0033 (3) | 0.0022 (3) | 0.0002 (3) |
O1 | 0.0307 (14) | 0.0182 (13) | 0.0257 (15) | 0.0037 (10) | 0.0031 (11) | −0.0061 (11) |
O2 | 0.0322 (15) | 0.0251 (14) | 0.0160 (14) | 0.0029 (11) | 0.0009 (10) | 0.0055 (11) |
O3 | 0.0403 (16) | 0.0382 (17) | 0.0280 (17) | −0.0053 (13) | 0.0023 (12) | 0.0112 (14) |
O4 | 0.0468 (18) | 0.0483 (19) | 0.0276 (17) | −0.0252 (14) | 0.0044 (13) | −0.0050 (14) |
N1 | 0.0314 (18) | 0.0155 (16) | 0.0247 (19) | −0.0008 (13) | 0.0120 (13) | −0.0028 (13) |
N2 | 0.0231 (15) | 0.0191 (16) | 0.0148 (17) | 0.0006 (12) | −0.0004 (11) | −0.0027 (13) |
N3 | 0.0277 (18) | 0.0256 (17) | 0.0220 (19) | 0.0001 (13) | 0.0067 (13) | −0.0017 (14) |
C1 | 0.0256 (19) | 0.0141 (18) | 0.017 (2) | −0.0029 (13) | 0.0096 (13) | −0.0001 (14) |
C2 | 0.030 (2) | 0.0205 (19) | 0.015 (2) | 0.0007 (14) | 0.0023 (14) | 0.0000 (15) |
C3 | 0.032 (2) | 0.022 (2) | 0.019 (2) | 0.0021 (15) | 0.0053 (15) | 0.0035 (16) |
C4 | 0.029 (2) | 0.0226 (19) | 0.016 (2) | −0.0038 (15) | 0.0052 (14) | −0.0004 (15) |
C5 | 0.0251 (19) | 0.0208 (19) | 0.0166 (19) | 0.0009 (14) | 0.0016 (14) | 0.0026 (15) |
C6 | 0.0191 (18) | 0.0209 (19) | 0.016 (2) | 0.0038 (13) | 0.0030 (13) | −0.0014 (14) |
C7 | 0.0237 (19) | 0.029 (2) | 0.0108 (18) | 0.0007 (15) | 0.0006 (13) | 0.0008 (15) |
C8 | 0.0214 (19) | 0.026 (2) | 0.016 (2) | 0.0010 (14) | 0.0002 (14) | −0.0045 (15) |
C9 | 0.0204 (18) | 0.0223 (19) | 0.021 (2) | 0.0028 (14) | 0.0071 (14) | −0.0008 (15) |
C10 | 0.026 (2) | 0.027 (2) | 0.0127 (19) | 0.0015 (15) | 0.0040 (14) | −0.0007 (15) |
C11 | 0.026 (2) | 0.027 (2) | 0.017 (2) | 0.0007 (15) | 0.0013 (14) | −0.0041 (15) |
Cl1 | 0.0313 (5) | 0.0241 (5) | 0.0291 (6) | −0.0098 (4) | 0.0022 (4) | 0.0005 (4) |
Cl2 | 0.0349 (6) | 0.0404 (6) | 0.0364 (7) | 0.0111 (4) | 0.0135 (4) | −0.0022 (5) |
Cl3 | 0.0325 (5) | 0.0345 (6) | 0.0187 (5) | −0.0087 (4) | −0.0031 (4) | 0.0073 (4) |
O5 | 0.0286 (14) | 0.0216 (14) | 0.0182 (15) | −0.0052 (10) | 0.0010 (10) | 0.0034 (10) |
O6 | 0.0330 (15) | 0.0242 (14) | 0.0209 (15) | −0.0064 (11) | −0.0021 (11) | 0.0070 (11) |
C12 | 0.0234 (19) | 0.0205 (19) | 0.020 (2) | −0.0016 (14) | 0.0040 (14) | 0.0010 (15) |
C13 | 0.0238 (18) | 0.0173 (18) | 0.0130 (19) | 0.0004 (14) | 0.0031 (13) | −0.0033 (14) |
S1—O2 | 1.435 (2) | C4—H4 | 0.9300 |
S1—O1 | 1.436 (3) | C5—H5 | 0.9300 |
S1—N2 | 1.631 (3) | C6—C11 | 1.388 (5) |
S1—C6 | 1.766 (4) | C6—C7 | 1.388 (5) |
O3—N3 | 1.231 (4) | C7—C8 | 1.394 (5) |
O4—N3 | 1.227 (4) | C7—H7 | 0.9300 |
N1—C4 | 1.335 (5) | C8—C9 | 1.372 (5) |
N1—C3 | 1.341 (5) | C8—H8 | 0.9300 |
N1—H1 | 0.897 (10) | C9—C10 | 1.387 (5) |
N2—C1 | 1.390 (4) | C10—C11 | 1.386 (5) |
N2—H2 | 0.897 (10) | C10—H10 | 0.9300 |
N3—C9 | 1.472 (5) | C11—H11 | 0.9300 |
C1—C2 | 1.397 (5) | Cl1—C12 | 1.765 (4) |
C1—C5 | 1.405 (5) | Cl2—C12 | 1.777 (4) |
C2—C3 | 1.362 (5) | Cl3—C12 | 1.770 (4) |
C2—H2A | 0.9300 | O5—C13 | 1.245 (4) |
C3—H3 | 0.9300 | O6—C13 | 1.231 (4) |
C4—C5 | 1.368 (5) | C12—C13 | 1.570 (4) |
O2—S1—O1 | 120.25 (15) | C1—C5—H5 | 120.6 |
O2—S1—N2 | 109.93 (16) | C11—C6—C7 | 121.7 (3) |
O1—S1—N2 | 104.59 (14) | C11—C6—S1 | 118.4 (3) |
O2—S1—C6 | 107.91 (16) | C7—C6—S1 | 119.7 (3) |
O1—S1—C6 | 109.75 (17) | C6—C7—C8 | 118.9 (3) |
N2—S1—C6 | 103.08 (16) | C6—C7—H7 | 120.5 |
C4—N1—C3 | 121.4 (3) | C8—C7—H7 | 120.5 |
C4—N1—H1 | 113 (2) | C9—C8—C7 | 118.2 (3) |
C3—N1—H1 | 126 (2) | C9—C8—H8 | 120.9 |
C1—N2—S1 | 124.7 (2) | C7—C8—H8 | 120.9 |
C1—N2—H2 | 123 (3) | C8—C9—C10 | 123.9 (3) |
S1—N2—H2 | 112 (3) | C8—C9—N3 | 118.4 (3) |
O4—N3—O3 | 124.1 (3) | C10—C9—N3 | 117.7 (3) |
O4—N3—C9 | 117.4 (3) | C11—C10—C9 | 117.4 (3) |
O3—N3—C9 | 118.4 (3) | C11—C10—H10 | 121.3 |
N2—C1—C2 | 118.2 (3) | C9—C10—H10 | 121.3 |
N2—C1—C5 | 123.4 (3) | C10—C11—C6 | 119.8 (3) |
C2—C1—C5 | 118.4 (3) | C10—C11—H11 | 120.1 |
C3—C2—C1 | 119.7 (3) | C6—C11—H11 | 120.1 |
C3—C2—H2A | 120.2 | C13—C12—Cl1 | 110.7 (2) |
C1—C2—H2A | 120.2 | C13—C12—Cl3 | 112.9 (3) |
N1—C3—C2 | 120.5 (3) | Cl1—C12—Cl3 | 109.12 (19) |
N1—C3—H3 | 119.7 | C13—C12—Cl2 | 105.4 (2) |
C2—C3—H3 | 119.7 | Cl1—C12—Cl2 | 109.6 (2) |
N1—C4—C5 | 121.1 (3) | Cl3—C12—Cl2 | 108.90 (19) |
N1—C4—H4 | 119.5 | O6—C13—O5 | 127.6 (3) |
C5—C4—H4 | 119.5 | O6—C13—C12 | 115.6 (3) |
C4—C5—C1 | 118.8 (3) | O5—C13—C12 | 116.8 (3) |
C4—C5—H5 | 120.6 | ||
O2—S1—N2—C1 | −62.4 (3) | S1—C6—C7—C8 | 175.1 (3) |
O1—S1—N2—C1 | 167.2 (3) | C6—C7—C8—C9 | 0.4 (5) |
C6—S1—N2—C1 | 52.4 (3) | C7—C8—C9—C10 | 0.8 (6) |
S1—N2—C1—C2 | −148.4 (3) | C7—C8—C9—N3 | −177.4 (3) |
S1—N2—C1—C5 | 32.5 (5) | O4—N3—C9—C8 | −11.3 (5) |
N2—C1—C2—C3 | −178.7 (3) | O3—N3—C9—C8 | 169.0 (3) |
C5—C1—C2—C3 | 0.4 (5) | O4—N3—C9—C10 | 170.3 (3) |
C4—N1—C3—C2 | 0.3 (6) | O3—N3—C9—C10 | −9.4 (5) |
C1—C2—C3—N1 | −0.3 (6) | C8—C9—C10—C11 | −1.8 (6) |
C3—N1—C4—C5 | −0.4 (6) | N3—C9—C10—C11 | 176.4 (3) |
N1—C4—C5—C1 | 0.6 (6) | C9—C10—C11—C6 | 1.6 (5) |
N2—C1—C5—C4 | 178.5 (3) | C7—C6—C11—C10 | −0.4 (5) |
C2—C1—C5—C4 | −0.6 (5) | S1—C6—C11—C10 | −176.2 (3) |
O2—S1—C6—C11 | −174.3 (3) | Cl1—C12—C13—O6 | 37.9 (4) |
O1—S1—C6—C11 | −41.5 (3) | Cl3—C12—C13—O6 | 160.6 (3) |
N2—S1—C6—C11 | 69.5 (3) | Cl2—C12—C13—O6 | −80.6 (3) |
O2—S1—C6—C7 | 9.9 (3) | Cl1—C12—C13—O5 | −144.5 (3) |
O1—S1—C6—C7 | 142.6 (3) | Cl3—C12—C13—O5 | −21.8 (4) |
N2—S1—C6—C7 | −106.4 (3) | Cl2—C12—C13—O5 | 97.0 (3) |
C11—C6—C7—C8 | −0.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.90 (1) | 1.76 (1) | 2.639 (4) | 168 (4) |
N2—H2···O6ii | 0.90 (1) | 1.83 (2) | 2.707 (4) | 167 (4) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C11H10N3O4S·C2Cl3O2 |
Mr | 442.65 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 22.017 (4), 6.2187 (12), 12.719 (3) |
β (°) | 97.48 (3) |
V (Å3) | 1726.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.14 × 0.12 × 0.04 |
Data collection | |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.910, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9585, 3017, 2440 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.162, 1.16 |
No. of reflections | 3017 |
No. of parameters | 243 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.54 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.897 (10) | 1.755 (13) | 2.639 (4) | 168 (4) |
N2—H2···O6ii | 0.897 (10) | 1.825 (15) | 2.707 (4) | 167 (4) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y+1, z. |
References
El-Naggar, A. M., Ahmed, F. S. M. & Badie, M. F. (1981). J. Heterocycl. Chem. 18, 91–94. CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA . Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Talley, J. J., Brown, D. L., Carter, J. S., Graneto, M. J., Koboldt, C. M., Masferrer, J. L., Perkins, W. E., Rogers, R. S., Shaffer, A. F., Zhang, Y. Y., Zweifel, B. S. & Seibert, K. (2000). J. Med. Chem. 43, 775–777. Web of Science CrossRef PubMed CAS Google Scholar
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Benzenesulfonamides are very important intermediates in the organic synthesis and are widely used for the synthesis of pharmaceutical compounds (Talley et al., 2000). In our ongoing investigations on this topic we characterize the the title compound by single-crystal X-ray diffraction. In its crystal structure the dihedral angle between the phenyl and the pyridinyl ring amount to 69.2 (1)°. The 4-nitro-N-(pyridinium-4-yl)benzenesulfonamide cations and the trichloroacetate anions are connected by intermolecular N—H···O hydrogen bonding between the N—H atoms of the cations and the oxygen atoms of the anions.