4-(4-Nitro­benzene­sulfonamido)pyridinium trichloro­acetate

In the crystal structure of the title compound, C₁₁H₁₀N₃O₄S·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.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.162
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.90(3), Rep   0.897(10) ......       3.00 su-Ra
              N1   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.90(4), Rep   0.897(10) ......       4.00 su-Ra
              N2   -H2      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(3), Rep   0.897(10) ......       3.00 su-Ra
              N1   -H1      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(4), Rep   0.897(10) ......       4.00 su-Ra
              N2   -H2      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.75(3), Rep   1.755(13) ......       2.31 su-Ra
              H1   -O5      1.555   4.565
PLAT736_ALERT_1_C H...A   Calc     1.82(4), Rep   1.825(15) ......       2.67 su-Ra
              H2   -O6      1.555   1.565

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   8 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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.

Related literature

For related literature, see: Talley et al. (2000); El-Naggar et al. (1981).

S2. Experimental

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.

S3. Refinement

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.

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: 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).

Figures

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.

4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate

Crystal data

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) Å^3	Lamellar, colorless
Z = 4	0.14 × 0.12 × 0.04 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0873P)^2] where P = (Fo^2 + 2Fc^2)/3
3017 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.57 e Å^−3
2 restraints	Δρmin = −0.54 e Å^−3

Special details

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 (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5^i	0.90 (1)	1.76 (1)	2.639 (4)	168 (4)
N2—H2···O6^ii	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.