2-Chloro-N-(3-meth­oxy­benzo­yl)benzene­sulfonamide

In the title compound, C₁₄H₁₂ClNO₄S, the dihedral angle between the chloro- and meth­oxy-substituted benzene rings is 87.40 (1)°. In the crystal, adjacent mol­ecules form inversion-related dimers through strong N—H...O hydrogen bonds, generating R₂²(8) loops. The dimers are further connected through two C—H...O inter­actions that form C(11) chains and R₂²(14) loops. Aromatic π–π stacking inter­actions [centroid–centroid separation = 3.8574 (1) Å] are also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.101
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         40 Ang3
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          66 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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
   1 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
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: SS and BSPM analyzed the data. GRM and NRM synthesized and characterized the compound. VK collected the crystal data and PAS solved the structure and prepared the material.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Comment

As a part of the efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Gowda et al., 2010), the crystal structure of the title compound (I) was determined.

In the molecule, the conformation between the N—H bond and the ortho-chloro group in the sulfonyl bound benzene ring is syn. This is similar to that observed in N-(benzoyl)-2-chlorobenzenesulfonamide (II, Gowda et al. 2010).

In the structure, the adjacent molecules form inversion related dimers through strong N—H···O hydrogen bonds, generating R₂²(8) loops. The dimers are further connected through intermolecular C3—H3···O3 and C5—H5···O3 interactions that form C(11) chains and R₂²(14) loops. Aromatic π-π stacking interactions (centroid-centroid separation = 3.8574 (1) Å) are also observed in the structure.

Related literature

For a similar structure, see: Gowda et al. (2010)

S2. Experimental

The title compound was prepared by refluxing a mixture of 3-methoxybenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride (POCl₃) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point (443 K).

Colorless prisms of (I) were obtained from a slow evaporation of its ethanolic solution at room temperature.

S3. Refinement

The H atom of the NH group was located in a difference map and later refined freely. 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 or 1.5 times of the U_eq of the parent atom).

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) forming R2^2(8) loops and C(11) chains.
	Fig. 3. Molecular packing of (I) forming R2^2(14) loops.
	Fig. 4. Stacking of molecules through Cg···Cg interactions. Cg is the centroid of the methoxy substituted benzene ring.

2-Chloro-N-(3-methoxybenzoyl)benzenesulfonamide

Crystal data

C14H12ClNO4S	F(000) = 336
Mr = 325.76	Prism
Triclinic, P1	Dx = 1.473 Mg m^−3
Hall symbol: -P 1	Melting point: 443 K
a = 7.5731 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1861 (5) Å	Cell parameters from 1029 reflections
c = 10.3636 (6) Å	θ = 2.7–25.0°
α = 94.945 (4)°	µ = 0.42 mm^−1
β = 96.581 (5)°	T = 293 K
γ = 110.974 (5)°	Prism, colourless
V = 734.56 (7) Å^3	0.35 × 0.28 × 0.22 mm
Z = 2

Data collection

Bruker APEXII diffractometer	Rint = 0.038
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.7°
Graphite monochromator	h = −8→8
phi and ω scans	k = −12→12
11351 measured reflections	l = −12→12
2584 independent reflections	2 standard reflections every 1 reflections
2133 reflections with I > 2σ(I)	intensity decay: 10%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.1773P] where P = (Fo^2 + 2Fc^2)/3
2584 reflections	(Δ/σ)max = 0.006
195 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
HN1	0.513 (4)	0.639 (3)	0.931 (3)	0.057 (8)*
C1	0.2590 (3)	0.4163 (2)	0.67778 (18)	0.0355 (5)
C2	0.4118 (3)	0.3814 (2)	0.6470 (2)	0.0404 (5)
C3	0.4049 (4)	0.3179 (3)	0.5217 (2)	0.0514 (6)
H3	0.5072	0.2947	0.5005	0.062*
C4	0.2458 (4)	0.2894 (3)	0.4285 (2)	0.0566 (7)
H4	0.2411	0.2460	0.3448	0.068*
C5	0.0939 (4)	0.3242 (3)	0.4578 (2)	0.0547 (6)
H5	−0.0122	0.3051	0.3940	0.066*
C6	0.0999 (3)	0.3876 (2)	0.5822 (2)	0.0450 (5)
H6	−0.0025	0.4111	0.6024	0.054*
C7	0.4531 (3)	0.7563 (2)	0.8139 (2)	0.0385 (5)
C8	0.6044 (3)	0.8929 (2)	0.8800 (2)	0.0390 (5)
C9	0.6794 (3)	0.9116 (2)	1.0120 (2)	0.0402 (5)
H9	0.6398	0.8371	1.0612	0.048*
C10	0.8142 (3)	1.0429 (2)	1.0698 (2)	0.0450 (5)
C11	0.8727 (3)	1.1534 (2)	0.9965 (3)	0.0533 (6)
H11	0.9626	1.2412	1.0355	0.064*
C12	0.7984 (4)	1.1338 (3)	0.8665 (3)	0.0585 (7)
H12	0.8384	1.2087	0.8177	0.070*
C13	0.6639 (3)	1.0035 (2)	0.8062 (2)	0.0506 (6)
H13	0.6146	0.9907	0.7176	0.061*
C14	0.8344 (4)	0.9647 (3)	1.2797 (3)	0.0710 (8)
H14A	0.6997	0.9395	1.2805	0.106*
H14B	0.9025	0.9995	1.3673	0.106*
H14C	0.8580	0.8825	1.2465	0.106*
O1	0.2842 (2)	0.39742 (15)	0.92753 (14)	0.0450 (4)
O2	0.0743 (2)	0.51231 (17)	0.83161 (15)	0.0508 (4)
O3	0.3527 (2)	0.74552 (17)	0.70992 (15)	0.0526 (4)
O4	0.8980 (3)	1.07160 (17)	1.19821 (17)	0.0628 (5)
S1	0.24743 (7)	0.48701 (5)	0.83723 (5)	0.03761 (17)
N1	0.4298 (3)	0.63820 (18)	0.87817 (18)	0.0398 (4)
Cl1	0.61560 (9)	0.41609 (7)	0.75991 (6)	0.0578 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0390 (12)	0.0294 (10)	0.0326 (10)	0.0097 (9)	−0.0032 (9)	0.0000 (8)
C2	0.0387 (13)	0.0383 (12)	0.0398 (11)	0.0116 (10)	−0.0013 (9)	0.0044 (9)
C3	0.0547 (15)	0.0508 (14)	0.0481 (13)	0.0199 (12)	0.0083 (11)	0.0019 (11)
C4	0.0656 (18)	0.0565 (15)	0.0368 (12)	0.0152 (13)	−0.0003 (11)	−0.0072 (11)
C5	0.0583 (16)	0.0535 (15)	0.0409 (13)	0.0166 (13)	−0.0149 (11)	−0.0053 (11)
C6	0.0412 (13)	0.0404 (12)	0.0469 (13)	0.0134 (10)	−0.0088 (10)	0.0000 (10)
C7	0.0385 (12)	0.0381 (12)	0.0400 (11)	0.0164 (10)	0.0054 (9)	0.0027 (9)
C8	0.0383 (12)	0.0318 (11)	0.0489 (12)	0.0145 (9)	0.0096 (10)	0.0056 (9)
C9	0.0384 (12)	0.0303 (11)	0.0499 (13)	0.0110 (9)	0.0064 (10)	0.0030 (9)
C10	0.0380 (13)	0.0344 (12)	0.0598 (14)	0.0123 (10)	0.0065 (10)	−0.0022 (10)
C11	0.0426 (14)	0.0327 (12)	0.0795 (18)	0.0084 (10)	0.0126 (12)	0.0023 (12)
C12	0.0550 (16)	0.0392 (13)	0.0849 (19)	0.0141 (12)	0.0252 (14)	0.0237 (13)
C13	0.0508 (15)	0.0462 (14)	0.0584 (14)	0.0196 (12)	0.0124 (11)	0.0142 (11)
C14	0.079 (2)	0.0590 (17)	0.0580 (16)	0.0125 (15)	−0.0047 (14)	−0.0001 (13)
O1	0.0472 (9)	0.0376 (8)	0.0398 (8)	0.0055 (7)	−0.0025 (7)	0.0085 (6)
O2	0.0379 (9)	0.0558 (10)	0.0545 (9)	0.0164 (8)	0.0025 (7)	−0.0040 (8)
O3	0.0556 (10)	0.0529 (10)	0.0475 (9)	0.0212 (8)	−0.0036 (8)	0.0079 (7)
O4	0.0652 (12)	0.0421 (10)	0.0614 (11)	0.0051 (9)	−0.0064 (9)	−0.0090 (8)
S1	0.0354 (3)	0.0351 (3)	0.0362 (3)	0.0091 (2)	−0.0017 (2)	0.0003 (2)
N1	0.0388 (11)	0.0319 (10)	0.0411 (10)	0.0091 (8)	−0.0079 (8)	0.0010 (8)
Cl1	0.0433 (4)	0.0770 (5)	0.0540 (4)	0.0283 (3)	−0.0046 (3)	0.0028 (3)

Geometric parameters (Å, º)

C1—C2	1.388 (3)	C9—C10	1.390 (3)
C1—C6	1.394 (3)	C9—H9	0.9300
C1—S1	1.769 (2)	C10—O4	1.365 (3)
C2—C3	1.387 (3)	C10—C11	1.382 (3)
C2—Cl1	1.732 (2)	C11—C12	1.368 (4)
C3—C4	1.379 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—C5	1.376 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (3)	C14—O4	1.417 (3)
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—O3	1.218 (2)	C14—H14C	0.9600
C7—N1	1.391 (3)	O1—S1	1.4337 (14)
C7—C8	1.494 (3)	O2—S1	1.4200 (16)
C8—C13	1.386 (3)	S1—N1	1.6402 (18)
C8—C9	1.389 (3)	N1—HN1	0.79 (3)
C2—C1—C6	119.67 (19)	O4—C10—C9	123.9 (2)
C2—C1—S1	123.23 (15)	C11—C10—C9	120.2 (2)
C6—C1—S1	116.98 (17)	C12—C11—C10	120.0 (2)
C3—C2—C1	119.8 (2)	C12—C11—H11	120.0
C3—C2—Cl1	117.89 (18)	C10—C11—H11	120.0
C1—C2—Cl1	122.28 (16)	C11—C12—C13	120.9 (2)
C4—C3—C2	119.8 (2)	C11—C12—H12	119.5
C4—C3—H3	120.1	C13—C12—H12	119.5
C2—C3—H3	120.1	C8—C13—C12	119.1 (2)
C5—C4—C3	120.9 (2)	C8—C13—H13	120.5
C5—C4—H4	119.5	C12—C13—H13	120.5
C3—C4—H4	119.5	O4—C14—H14A	109.5
C4—C5—C6	119.7 (2)	O4—C14—H14B	109.5
C4—C5—H5	120.2	H14A—C14—H14B	109.5
C6—C5—H5	120.2	O4—C14—H14C	109.5
C5—C6—C1	120.2 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.9	H14B—C14—H14C	109.5
C1—C6—H6	119.9	C10—O4—C14	118.15 (18)
O3—C7—N1	120.3 (2)	O2—S1—O1	119.16 (10)
O3—C7—C8	123.37 (19)	O2—S1—N1	109.37 (10)
N1—C7—C8	116.29 (18)	O1—S1—N1	104.24 (9)
C13—C8—C9	120.4 (2)	O2—S1—C1	107.73 (10)
C13—C8—C7	117.8 (2)	O1—S1—C1	108.22 (9)
C9—C8—C7	121.78 (19)	N1—S1—C1	107.61 (10)
C8—C9—C10	119.4 (2)	C7—N1—S1	123.60 (15)
C8—C9—H9	120.3	C7—N1—HN1	119.7 (19)
C10—C9—H9	120.3	S1—N1—HN1	116.2 (19)
O4—C10—C11	115.9 (2)
C6—C1—C2—C3	−0.1 (3)	O4—C10—C11—C12	179.1 (2)
S1—C1—C2—C3	175.85 (17)	C9—C10—C11—C12	−0.2 (4)
C6—C1—C2—Cl1	179.10 (16)	C10—C11—C12—C13	0.0 (4)
S1—C1—C2—Cl1	−4.9 (3)	C9—C8—C13—C12	−0.6 (3)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C13—C12	177.2 (2)
Cl1—C2—C3—C4	−179.55 (18)	C11—C12—C13—C8	0.4 (4)
C2—C3—C4—C5	0.6 (4)	C11—C10—O4—C14	176.2 (2)
C3—C4—C5—C6	−0.5 (4)	C9—C10—O4—C14	−4.5 (3)
C4—C5—C6—C1	0.1 (4)	C2—C1—S1—O2	178.82 (17)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O2	−5.11 (19)
S1—C1—C6—C5	−175.99 (18)	C2—C1—S1—O1	−51.1 (2)
O3—C7—C8—C13	−15.7 (3)	C6—C1—S1—O1	124.97 (16)
N1—C7—C8—C13	164.6 (2)	C2—C1—S1—N1	60.99 (19)
O3—C7—C8—C9	162.0 (2)	C6—C1—S1—N1	−122.94 (17)
N1—C7—C8—C9	−17.6 (3)	O3—C7—N1—S1	−11.6 (3)
C13—C8—C9—C10	0.4 (3)	C8—C7—N1—S1	167.99 (15)
C7—C8—C9—C10	−177.34 (19)	O2—S1—N1—C7	−52.2 (2)
C8—C9—C10—O4	−179.3 (2)	O1—S1—N1—C7	179.30 (18)
C8—C9—C10—C11	0.0 (3)	C1—S1—N1—C7	64.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1^i	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5···O3^ii	0.93	2.53	3.417 (3)	160
C3—H3···O3^iii	0.93	2.60	3.338 (3)	137

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.