N-(3-Chloro­benzo­yl)-3-nitro­benzene­sulfonamide

In the title compound, C₁₃H₉ClN₂O₅S, the dihedral angle between the two benzene rings is 83.5 (1)°. In the crystal, mol­ecules are linked via N—H...O(S) hydrogen bonds into helical chains running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.105
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0054 Ang
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O4      ..       3.12 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         24
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         27

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2011) and N-chloro-arylsulfonamides (Gowda & Mahadevappa, 1983), in the present work, the crystal structure of N-(3-chlorobenzoyl)-3-nitrobenzenesulfonamide (I) has been determined (Fig.1).

The conformation between the N—H and C=O bonds in the C—SO₂—NH—C(O) segment is anti and the N—C bond in the segment has gauche torsion with respect to the S═O bonds(Fig.1), similar to that observed in N-(benzoyl)-3-nitrobenzenesulfonamide (II)(Suchetan et al., 2011). Further, in (I), the conformation between the N—H bond and the meta-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (II). But the conformation of the C═O is anti to the meta-Cl atom in the benzoyl ring.

The molecule is twisted at the S—N bond with the torsional angle of -60.40 (29)°, compared to the value of -62.80 (17)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 77.0 (1)°, compared to the value of 79.2 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 83.5 (1)°, compared to the value of 86.7 (1)° in (II).

The packing of molecules linked by of N—H···O(S) hydrogen bonds(Table 1) is shown in Fig. 2.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2004), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), onN-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983).

S2. Experimental

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 3-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)-3-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

S3. Refinement

The H atom of the NH group was located in a difference map and its coordinates were refined with the N—H distance restrained to 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the U_eq of the parent atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(3-Chlorobenzoyl)-3-nitrobenzenesulfonamide

Crystal data

C13H9ClN2O5S	F(000) = 696
Mr = 340.73	Dx = 1.602 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1638 reflections
a = 11.891 (2) Å	θ = 2.4–27.9°
b = 5.0577 (6) Å	µ = 0.44 mm^−1
c = 23.488 (3) Å	T = 293 K
β = 90.43 (1)°	Rod, colourless
V = 1412.6 (3) Å^3	0.46 × 0.20 × 0.10 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2840 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.822, Tmax = 0.957	k = −3→6
4873 measured reflections	l = −14→29

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0074P)^2 + 2.6391P] where P = (Fo^2 + 2Fc^2)/3
2840 reflections	(Δ/σ)max = 0.005
202 parameters	Δρmax = 0.35 e Å^−3
1 restraint	Δρmin = −0.35 e Å^−3

Special details

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	−0.01505 (9)	0.2312 (2)	0.06480 (5)	0.0673 (3)
S1	0.16424 (7)	1.19021 (16)	0.25405 (3)	0.0329 (2)
O1	0.1952 (2)	1.4485 (5)	0.23632 (10)	0.0459 (6)
O2	0.06284 (18)	1.1510 (5)	0.28538 (9)	0.0426 (6)
O3	0.3210 (2)	1.0853 (6)	0.16263 (11)	0.0549 (7)
O4	0.2384 (3)	0.4415 (6)	0.40468 (13)	0.0754 (9)
O5	0.4054 (3)	0.4980 (8)	0.43876 (14)	0.0927 (12)
N1	0.1495 (2)	0.9973 (5)	0.19807 (11)	0.0326 (6)
H1N	0.099 (2)	0.888 (6)	0.2022 (14)	0.039*
N2	0.3285 (3)	0.5553 (7)	0.40604 (14)	0.0596 (10)
C1	0.2775 (3)	1.0595 (6)	0.29449 (13)	0.0329 (7)
C2	0.2570 (3)	0.8591 (7)	0.33282 (14)	0.0369 (8)
H2	0.1858	0.7855	0.3366	0.044*
C3	0.3472 (3)	0.7720 (7)	0.36558 (14)	0.0427 (9)
C4	0.4536 (3)	0.8782 (9)	0.36104 (16)	0.0529 (10)
H4	0.5124	0.8157	0.3836	0.063*
C5	0.4710 (3)	1.0782 (9)	0.32241 (17)	0.0540 (10)
H5	0.5423	1.1519	0.3189	0.065*
C6	0.3836 (3)	1.1707 (8)	0.28888 (15)	0.0436 (8)
H6	0.3957	1.3060	0.2628	0.052*
C7	0.2344 (3)	0.9602 (7)	0.15852 (14)	0.0373 (8)
C8	0.2142 (3)	0.7600 (7)	0.11301 (13)	0.0374 (8)
C9	0.1165 (3)	0.6101 (7)	0.10919 (14)	0.0399 (8)
H9	0.0580	0.6387	0.1345	0.048*
C10	0.1067 (3)	0.4200 (8)	0.06786 (14)	0.0451 (9)
C11	0.1915 (4)	0.3747 (9)	0.02952 (15)	0.0571 (11)
H11	0.1840	0.2445	0.0018	0.069*
C12	0.2877 (4)	0.5261 (9)	0.03305 (16)	0.0607 (12)
H12	0.3454	0.4976	0.0072	0.073*
C13	0.3000 (3)	0.7185 (8)	0.07404 (14)	0.0473 (9)
H13	0.3651	0.8202	0.0757	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0696 (7)	0.0659 (7)	0.0663 (7)	−0.0096 (6)	−0.0136 (5)	−0.0209 (6)
S1	0.0345 (4)	0.0284 (4)	0.0357 (4)	0.0021 (4)	0.0005 (3)	−0.0003 (4)
O1	0.0571 (16)	0.0278 (13)	0.0526 (15)	−0.0010 (11)	−0.0058 (12)	0.0028 (11)
O2	0.0355 (12)	0.0516 (15)	0.0408 (13)	0.0068 (11)	0.0062 (10)	−0.0020 (12)
O3	0.0418 (14)	0.0674 (18)	0.0557 (16)	−0.0170 (14)	0.0096 (12)	−0.0107 (15)
O4	0.093 (2)	0.062 (2)	0.072 (2)	0.0072 (19)	0.0132 (19)	0.0273 (18)
O5	0.104 (3)	0.108 (3)	0.066 (2)	0.040 (2)	−0.0120 (19)	0.031 (2)
N1	0.0338 (15)	0.0324 (15)	0.0318 (14)	−0.0039 (12)	0.0040 (12)	−0.0014 (12)
N2	0.081 (3)	0.058 (2)	0.0409 (18)	0.031 (2)	0.0058 (19)	0.0080 (17)
C1	0.0352 (17)	0.0316 (17)	0.0320 (16)	0.0022 (14)	0.0005 (13)	−0.0031 (15)
C2	0.0380 (18)	0.0339 (19)	0.0388 (18)	0.0029 (15)	0.0026 (14)	−0.0020 (15)
C3	0.054 (2)	0.042 (2)	0.0327 (17)	0.0148 (18)	0.0003 (15)	−0.0013 (16)
C4	0.047 (2)	0.066 (3)	0.045 (2)	0.020 (2)	−0.0072 (17)	−0.012 (2)
C5	0.0344 (19)	0.072 (3)	0.056 (2)	−0.002 (2)	−0.0006 (17)	−0.010 (2)
C6	0.0395 (19)	0.045 (2)	0.046 (2)	−0.0034 (17)	0.0036 (16)	−0.0016 (18)
C7	0.0375 (18)	0.0384 (19)	0.0360 (18)	0.0004 (16)	0.0017 (15)	0.0049 (15)
C8	0.0418 (18)	0.039 (2)	0.0313 (17)	0.0070 (16)	0.0047 (14)	0.0034 (15)
C9	0.0410 (19)	0.047 (2)	0.0314 (17)	0.0049 (17)	0.0038 (14)	−0.0014 (16)
C10	0.057 (2)	0.047 (2)	0.0319 (18)	0.0084 (18)	−0.0062 (16)	−0.0074 (17)
C11	0.077 (3)	0.060 (3)	0.035 (2)	0.014 (2)	−0.0030 (19)	−0.0113 (19)
C12	0.065 (3)	0.076 (3)	0.041 (2)	0.015 (2)	0.018 (2)	−0.005 (2)
C13	0.049 (2)	0.054 (2)	0.0388 (19)	0.0050 (19)	0.0087 (16)	0.0026 (19)

Geometric parameters (Å, º)

Cl1—C10	1.736 (4)	C4—C5	1.376 (6)
S1—O1	1.420 (2)	C4—H4	0.9300
S1—O2	1.431 (2)	C5—C6	1.381 (5)
S1—N1	1.645 (3)	C5—H5	0.9300
S1—C1	1.770 (3)	C6—H6	0.9300
O3—C7	1.212 (4)	C7—C8	1.490 (5)
O4—N2	1.217 (5)	C8—C9	1.390 (5)
O5—N2	1.225 (4)	C8—C13	1.391 (4)
N1—C7	1.390 (4)	C9—C10	1.371 (5)
N1—H1N	0.823 (18)	C9—H9	0.9300
N2—C3	1.468 (5)	C10—C11	1.376 (5)
C1—C2	1.378 (4)	C11—C12	1.379 (6)
C1—C6	1.388 (4)	C11—H11	0.9300
C2—C3	1.387 (5)	C12—C13	1.376 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.380 (5)	C13—H13	0.9300
O1—S1—O2	119.97 (15)	C6—C5—H5	119.7
O1—S1—N1	109.70 (15)	C5—C6—C1	119.3 (4)
O2—S1—N1	104.11 (14)	C5—C6—H6	120.4
O1—S1—C1	107.63 (15)	C1—C6—H6	120.4
O2—S1—C1	108.23 (15)	O3—C7—N1	119.8 (3)
N1—S1—C1	106.45 (14)	O3—C7—C8	123.0 (3)
C7—N1—S1	122.8 (2)	N1—C7—C8	117.2 (3)
C7—N1—H1N	121 (2)	C9—C8—C13	119.5 (3)
S1—N1—H1N	112 (2)	C9—C8—C7	123.1 (3)
O4—N2—O5	123.9 (4)	C13—C8—C7	117.4 (3)
O4—N2—C3	118.2 (3)	C10—C9—C8	119.6 (3)
O5—N2—C3	117.8 (4)	C10—C9—H9	120.2
C2—C1—C6	121.7 (3)	C8—C9—H9	120.2
C2—C1—S1	119.2 (2)	C9—C10—C11	121.5 (4)
C6—C1—S1	119.1 (3)	C9—C10—Cl1	118.8 (3)
C1—C2—C3	117.2 (3)	C11—C10—Cl1	119.8 (3)
C1—C2—H2	121.4	C10—C11—C12	118.7 (4)
C3—C2—H2	121.4	C10—C11—H11	120.7
C4—C3—C2	122.6 (3)	C12—C11—H11	120.7
C4—C3—N2	118.9 (3)	C13—C12—C11	121.2 (4)
C2—C3—N2	118.5 (3)	C13—C12—H12	119.4
C5—C4—C3	118.7 (3)	C11—C12—H12	119.4
C5—C4—H4	120.7	C12—C13—C8	119.5 (4)
C3—C4—H4	120.7	C12—C13—H13	120.2
C4—C5—C6	120.6 (4)	C8—C13—H13	120.2
C4—C5—H5	119.7
O1—S1—N1—C7	55.8 (3)	C4—C5—C6—C1	0.0 (6)
O2—S1—N1—C7	−174.6 (3)	C2—C1—C6—C5	0.1 (5)
C1—S1—N1—C7	−60.4 (3)	S1—C1—C6—C5	176.8 (3)
O1—S1—C1—C2	157.3 (3)	S1—N1—C7—O3	−4.7 (5)
O2—S1—C1—C2	26.2 (3)	S1—N1—C7—C8	174.1 (2)
N1—S1—C1—C2	−85.2 (3)	O3—C7—C8—C9	177.9 (3)
O1—S1—C1—C6	−19.5 (3)	N1—C7—C8—C9	−0.8 (5)
O2—S1—C1—C6	−150.5 (3)	O3—C7—C8—C13	0.0 (5)
N1—S1—C1—C6	98.1 (3)	N1—C7—C8—C13	−178.7 (3)
C6—C1—C2—C3	−0.2 (5)	C13—C8—C9—C10	1.3 (5)
S1—C1—C2—C3	−176.9 (2)	C7—C8—C9—C10	−176.5 (3)
C1—C2—C3—C4	0.2 (5)	C8—C9—C10—C11	−0.5 (5)
C1—C2—C3—N2	−178.9 (3)	C8—C9—C10—Cl1	178.8 (3)
O4—N2—C3—C4	−171.0 (4)	C9—C10—C11—C12	−0.3 (6)
O5—N2—C3—C4	8.2 (5)	Cl1—C10—C11—C12	−179.6 (3)
O4—N2—C3—C2	8.1 (5)	C10—C11—C12—C13	0.3 (6)
O5—N2—C3—C2	−172.7 (3)	C11—C12—C13—C8	0.6 (6)
C2—C3—C4—C5	−0.1 (5)	C9—C8—C13—C12	−1.4 (5)
N2—C3—C4—C5	179.0 (3)	C7—C8—C13—C12	176.6 (3)
C3—C4—C5—C6	0.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.82 (2)	2.29 (2)	3.100 (3)	169 (3)

Symmetry code: (i) −x, y−1/2, −z+1/2.