A triclinic polymorph of N-[4-(4-methyl­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

Hayat, K.; Asghar, M.N.; Tahir, M.N.; Shafiq, M.; Ahmad, D.

doi:10.1107/S1600536812008616

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o983-o984

doi:10.1107/S1600536812008616

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A triclinic polymorph of N-[4-(4-methylbenzenesulfonamido)phenylsulfonyl]acetamide

Khizar Hayat,^a Muhammad Nadeem Asghar,^a M. Nawaz Tahir,^b ^* Muhammad Shafiq ^c and Dildar Ahmad ^a

^aForman Christian College (A Chartered University), Ferozepur Road, Lahore 54600, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 3 February 2012; accepted 26 February 2012; online 7 March 2012)

In the asymmetric unit of the title compound, C₁₅H₁₆N₂O₅S₂, there are two symmetry-independent molecules which adopt similar conformations, with dihedral angles between the aromatic rings of 59.30 (8) and 61.81 (8)°, and dihedral angles between acetamide group and the benzene ring of 77.08 (10) and 78.40 (10)°. Each type of molecule forms similar one-dimensional polymeric structures extending along the b axis via N—H⋯O hydrogen bonds. These hydrogen bonds generate two types of centrosymmetric motifs, R₂²(8) and R₂²(20). Moreover C—H⋯O interactions assemble the molecules into a three-dimensional framework. The crystal structure was determined from a non-merohedral twin [ratio of the twin components = 0.322 (4):0.678 (4)].

Related literature

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₅S₂
M_r = 368.42
Triclinic, $[P \overline 1]$
a = 9.6722 (3) Å
b = 11.9968 (4) Å
c = 15.4784 (6) Å
α = 82.802 (2)°
β = 79.232 (1)°
γ = 89.653 (2)°
V = 1750.24 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.915, T_max = 0.938
31011 measured reflections
8382 independent reflections
5598 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.153
S = 1.02
8382 reflections
438 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.86	2.14	2.841 (3)	138
N2—H2A⋯O4ⁱⁱ	0.86	2.06	2.876 (3)	158
N3—H3A⋯O10ⁱⁱⁱ	0.86	2.18	2.859 (3)	136
N4—H4⋯O8^iv	0.86	2.05	2.867 (3)	157
C13—H13⋯O2	0.93	2.49	3.062 (4)	120
C22—H22A⋯O6^v	0.96	2.59	3.338 (5)	135
C24—H24⋯O6	0.93	2.46	3.026 (4)	119
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008616/gk2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008616/gk2456Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008616/gk2456Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized as a part of the series of sulfonamide derivatives. The aim of our research work is to find the potential sulfonamide derivatives possesing anti-microbial activity. The crystal structure of the monoclinic polymorph of the title compound has been reported earlier by Ashfaq et al. (2010). The molecules in the two polymorphs differ in conformation.

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the toluene group A (C1–C7), benzene ring B (C8–C13) and the acetamide group C (N2/C14/C15/O5) are planar with r. m. s. deviation of 0.0089 Å, 0.0080 Å and 0.0028 Å, respectively. The dihedral angles between A/B, A/C and B/C are 61.81 (8)°, 45.90 (14)° and 77.08 (10)°, respectively. In second molecule, the toluene group D (C16–C22), benzene ring E (C23–C28) and the acetamide group F (N4/C29/C30/O10) are planar with r. m. s. deviation of 0.0116 Å, 0.0066 Å and 0.0006 Å, respectively. The dihedral angles between D/E, D/F and E/F are 59.30 (8)°, 46.10 (14)° and 78.40 (10)°, respectively. The dihedral angle between two aromatic rings in its polymrph (Ashfaq et al., 2010) is 81.33 (6)° compared to 61.81 (8)° and 59.30 (8)°. In both molecules, there exist weak intramolecular H–bonding of C—H···O type (Table 1). Both molecules are dimerized themselves due to intermolecular H-bonding of N—H···O type forming R₂²(8) ring motifs (Bernstein et al., 1995). The dimers are interliked due to strong N—H···O type of H–bondings (Table 1, Fig. 2) and form R₂²(20) ring motifs.

Related literature top

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equal molar ratio of N-[(4-aminophenyl)sulfonyl]acetamide and p-toluene sulfonyl chloride was dissolved in 20 ml distilled water. The solution with pH = 8–9 adjusted using Na₂CO₃ (1 M) was stirrered at room temperature for 6 h. Progress of the reaction was monitored by the consumption of suspended p-toluene sulfonyl chloride. On completion, pH was adjusted to 2–3 using HCl (2 N). The precipitate formed was filtered, washed with ditilled water and recrystallized from methanol to afford colorless prisms with m.p. 385 K.

Structure description top

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers forming R₂²(8) ring motif and dimers are interlinked and complete R₂²(20) ring motif. The H-atoms not involved in hydrogen bonding have been omitted for clarity.

N-[4-(4-Methylbenzenesulfonamido)phenylsulfonyl]acetamide top

Crystal data top

C₁₅H₁₆N₂O₅S₂	Z = 4
M_r = 368.42	F(000) = 768
Triclinic, P1	D_x = 1.398 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6722 (3) Å	Cell parameters from 4587 reflections
b = 11.9968 (4) Å	θ = 1.7–25.0°
c = 15.4784 (6) Å	µ = 0.33 mm⁻¹
α = 82.802 (2)°	T = 296 K
β = 79.232 (1)°	Prism, colorless
γ = 89.653 (2)°	0.35 × 0.25 × 0.22 mm
V = 1750.24 (11) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	8382 independent reflections
Radiation source: fine-focus sealed tube	5598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 7.60 pixels mm^-1	θ_max = 28.3°, θ_min = 1.7°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.915, T_max = 0.938	l = −20→20
31011 measured reflections

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0652P)² + 0.7795P] where P = (F_o² + 2F_c²)/3
8382 reflections	(Δ/σ)_max = 0.001
438 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₅S₂	γ = 89.653 (2)°
M_r = 368.42	V = 1750.24 (11) Å³
Triclinic, P1	Z = 4
a = 9.6722 (3) Å	Mo Kα radiation
b = 11.9968 (4) Å	µ = 0.33 mm⁻¹
c = 15.4784 (6) Å	T = 296 K
α = 82.802 (2)°	0.35 × 0.25 × 0.22 mm
β = 79.232 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	8382 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5598 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.938	R_int = 0.028
31011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.52 e Å⁻³
8382 reflections	Δρ_min = −0.45 e Å⁻³
438 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	U_iso*/U_eq
S1	1.18463 (8)	0.05657 (7)	0.15628 (5)	0.0535 (3)
S2	0.84421 (7)	0.35232 (5)	0.49521 (5)	0.0415 (2)
O1	1.2489 (3)	−0.0454 (2)	0.13292 (16)	0.0730 (9)
O2	1.2545 (2)	0.1621 (2)	0.12469 (15)	0.0698 (8)
O3	0.70702 (19)	0.30834 (16)	0.53244 (14)	0.0515 (7)
O4	0.8603 (2)	0.46483 (15)	0.44956 (14)	0.0523 (7)
O5	0.8812 (2)	0.18161 (16)	0.64458 (14)	0.0585 (7)
N1	1.1577 (3)	0.0404 (2)	0.26522 (15)	0.0494 (8)
N2	0.9331 (2)	0.35691 (18)	0.57571 (15)	0.0441 (7)
C1	1.0166 (3)	0.0638 (3)	0.12810 (18)	0.0500 (9)
C2	0.9520 (4)	0.1664 (3)	0.1181 (2)	0.0687 (12)
C3	0.8155 (4)	0.1685 (4)	0.1015 (3)	0.0785 (16)
C4	0.7443 (4)	0.0727 (4)	0.0942 (2)	0.0710 (14)
C5	0.8117 (4)	−0.0286 (4)	0.1023 (2)	0.0747 (14)
C6	0.9484 (4)	−0.0339 (3)	0.1193 (2)	0.0650 (12)
C7	0.5962 (4)	0.0779 (5)	0.0770 (3)	0.107 (2)
C8	1.0824 (3)	0.1175 (2)	0.31772 (17)	0.0423 (8)
C9	0.9745 (3)	0.0768 (2)	0.38598 (18)	0.0464 (9)
C10	0.9013 (3)	0.1481 (2)	0.44060 (19)	0.0450 (8)
C11	0.9352 (3)	0.2614 (2)	0.42570 (17)	0.0380 (8)
C12	1.0441 (3)	0.3032 (2)	0.35796 (19)	0.0516 (10)
C13	1.1186 (3)	0.2313 (2)	0.3047 (2)	0.0562 (10)
C14	0.9428 (3)	0.2699 (2)	0.64153 (18)	0.0447 (9)
C15	1.0310 (4)	0.2954 (3)	0.7061 (2)	0.0662 (12)
S3	0.69039 (8)	0.54642 (6)	0.15666 (5)	0.0506 (2)
S4	0.34505 (7)	0.15067 (5)	0.49579 (5)	0.0415 (2)
O6	0.7593 (2)	0.4488 (2)	0.12796 (15)	0.0663 (8)
O7	0.7553 (2)	0.65458 (19)	0.12984 (16)	0.0685 (8)
O8	0.3612 (2)	0.05275 (15)	0.45035 (14)	0.0517 (7)
O9	0.20777 (19)	0.18511 (16)	0.53232 (14)	0.0522 (7)
O10	0.3820 (2)	0.27238 (17)	0.64627 (14)	0.0581 (7)
N3	0.6647 (3)	0.53153 (19)	0.26533 (15)	0.0473 (8)
N4	0.4330 (2)	0.11853 (18)	0.57696 (15)	0.0435 (7)
C16	0.5211 (3)	0.5480 (3)	0.13051 (18)	0.0494 (9)
C17	0.4500 (4)	0.6488 (3)	0.1236 (2)	0.0664 (12)
C18	0.3142 (4)	0.6490 (4)	0.1090 (3)	0.0805 (16)
C19	0.2471 (4)	0.5512 (4)	0.1003 (2)	0.0774 (16)
C20	0.3210 (4)	0.4524 (4)	0.1049 (2)	0.0762 (14)
C21	0.4574 (4)	0.4491 (3)	0.1199 (2)	0.0630 (11)
C22	0.0974 (4)	0.5515 (6)	0.0856 (3)	0.121 (3)
C23	0.5887 (3)	0.4391 (2)	0.31887 (17)	0.0412 (8)
C24	0.6247 (3)	0.3287 (2)	0.3074 (2)	0.0533 (10)
C25	0.5486 (3)	0.2412 (2)	0.36048 (19)	0.0506 (9)
C26	0.4380 (3)	0.2630 (2)	0.42648 (17)	0.0389 (8)
C27	0.4030 (3)	0.3724 (2)	0.43997 (19)	0.0457 (8)
C28	0.4781 (3)	0.4596 (2)	0.38568 (18)	0.0452 (8)
C29	0.4428 (3)	0.1842 (2)	0.64282 (18)	0.0450 (9)
C30	0.5321 (4)	0.1372 (3)	0.7070 (2)	0.0655 (11)
H1	1.19113	−0.01807	0.29175	0.0592*
H2	0.99857	0.23250	0.12244	0.0824*
H2A	0.97704	0.41865	0.57684	0.0530*
H3	0.77109	0.23718	0.09504	0.0937*
H5	0.76554	−0.09420	0.09641	0.0899*
H6	0.99324	−0.10250	0.12462	0.0780*
H7A	0.58829	0.14113	0.03363	0.1594*
H7B	0.53193	0.08598	0.13109	0.1594*
H7C	0.57375	0.01005	0.05524	0.1594*
H9	0.95104	0.00057	0.39512	0.0557*
H10	0.82975	0.12018	0.48707	0.0540*
H12	1.06666	0.37953	0.34857	0.0619*
H13	1.19302	0.25870	0.26004	0.0675*
H15A	1.08342	0.23020	0.72170	0.0989*
H15B	0.97142	0.31599	0.75833	0.0989*
H15C	1.09487	0.35648	0.67974	0.0989*
H3A	0.69879	0.58185	0.29084	0.0568*
H4	0.47630	0.05569	0.57835	0.0522*
H17	0.49406	0.71564	0.12870	0.0796*
H18	0.26661	0.71646	0.10498	0.0965*
H20	0.27760	0.38609	0.09762	0.0914*
H21	0.50538	0.38172	0.12281	0.0753*
H22A	0.09375	0.52163	0.03134	0.1804*
H22B	0.06371	0.62703	0.08201	0.1804*
H22C	0.03928	0.50590	0.13413	0.1804*
H24	0.70038	0.31417	0.26384	0.0640*
H25	0.57139	0.16744	0.35203	0.0608*
H27	0.32961	0.38673	0.48515	0.0548*
H28	0.45444	0.53331	0.39387	0.0542*
H30A	0.47464	0.09206	0.75606	0.0981*
H30B	0.57526	0.19760	0.72820	0.0981*
H30C	0.60386	0.09164	0.67805	0.0981*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0472 (4)	0.0611 (5)	0.0493 (4)	0.0080 (3)	−0.0011 (3)	−0.0085 (3)
S2	0.0363 (3)	0.0328 (3)	0.0565 (4)	0.0002 (3)	−0.0108 (3)	−0.0063 (3)
O1	0.0676 (15)	0.0839 (17)	0.0679 (15)	0.0294 (13)	−0.0038 (12)	−0.0259 (12)
O2	0.0589 (14)	0.0778 (16)	0.0642 (14)	−0.0104 (12)	0.0028 (11)	0.0026 (12)
O3	0.0348 (10)	0.0470 (11)	0.0718 (13)	−0.0029 (8)	−0.0058 (9)	−0.0101 (9)
O4	0.0540 (12)	0.0328 (10)	0.0723 (13)	0.0028 (8)	−0.0208 (10)	−0.0016 (9)
O5	0.0577 (13)	0.0408 (11)	0.0734 (14)	−0.0052 (10)	−0.0097 (10)	0.0028 (10)
N1	0.0536 (14)	0.0459 (13)	0.0485 (13)	0.0113 (11)	−0.0110 (11)	−0.0038 (10)
N2	0.0470 (13)	0.0358 (11)	0.0512 (13)	−0.0061 (10)	−0.0130 (10)	−0.0056 (10)
C1	0.0504 (16)	0.0572 (18)	0.0418 (15)	0.0054 (14)	−0.0056 (12)	−0.0088 (13)
C2	0.073 (2)	0.063 (2)	0.078 (2)	0.0111 (18)	−0.0283 (19)	−0.0188 (17)
C3	0.075 (2)	0.085 (3)	0.086 (3)	0.030 (2)	−0.033 (2)	−0.026 (2)
C4	0.057 (2)	0.105 (3)	0.0506 (19)	0.001 (2)	−0.0073 (15)	−0.0122 (19)
C5	0.073 (2)	0.085 (3)	0.065 (2)	−0.024 (2)	−0.0119 (18)	−0.0052 (19)
C6	0.074 (2)	0.061 (2)	0.058 (2)	0.0000 (18)	−0.0095 (17)	−0.0041 (15)
C7	0.064 (3)	0.174 (5)	0.083 (3)	−0.001 (3)	−0.019 (2)	−0.014 (3)
C8	0.0442 (14)	0.0397 (14)	0.0443 (14)	0.0046 (11)	−0.0120 (11)	−0.0054 (11)
C9	0.0491 (16)	0.0327 (13)	0.0562 (17)	−0.0046 (12)	−0.0066 (13)	−0.0058 (12)
C10	0.0404 (14)	0.0388 (14)	0.0536 (16)	−0.0057 (11)	−0.0042 (12)	−0.0036 (12)
C11	0.0360 (13)	0.0313 (12)	0.0484 (15)	−0.0019 (10)	−0.0116 (11)	−0.0057 (10)
C12	0.0583 (18)	0.0345 (14)	0.0574 (18)	−0.0089 (13)	−0.0008 (14)	−0.0027 (12)
C13	0.0577 (18)	0.0446 (16)	0.0587 (18)	−0.0117 (14)	0.0060 (14)	−0.0016 (13)
C14	0.0380 (14)	0.0435 (15)	0.0500 (16)	0.0057 (12)	−0.0003 (12)	−0.0076 (12)
C15	0.067 (2)	0.075 (2)	0.059 (2)	−0.0006 (18)	−0.0183 (16)	−0.0083 (16)
S3	0.0428 (4)	0.0556 (4)	0.0502 (4)	−0.0075 (3)	−0.0006 (3)	−0.0061 (3)
S4	0.0370 (3)	0.0335 (3)	0.0558 (4)	0.0017 (3)	−0.0102 (3)	−0.0105 (3)
O6	0.0583 (13)	0.0745 (15)	0.0614 (14)	0.0071 (11)	0.0061 (10)	−0.0172 (11)
O7	0.0567 (13)	0.0655 (14)	0.0760 (15)	−0.0230 (11)	−0.0049 (11)	0.0085 (11)
O8	0.0558 (12)	0.0375 (10)	0.0670 (13)	0.0009 (9)	−0.0179 (10)	−0.0167 (9)
O9	0.0357 (10)	0.0473 (11)	0.0733 (14)	0.0022 (8)	−0.0071 (9)	−0.0108 (9)
O10	0.0561 (12)	0.0486 (12)	0.0730 (14)	0.0048 (10)	−0.0105 (10)	−0.0238 (10)
N3	0.0508 (14)	0.0434 (12)	0.0499 (13)	−0.0085 (10)	−0.0123 (10)	−0.0094 (10)
N4	0.0463 (12)	0.0333 (11)	0.0522 (13)	0.0067 (10)	−0.0115 (10)	−0.0075 (9)
C16	0.0480 (16)	0.0589 (18)	0.0405 (15)	−0.0075 (14)	−0.0046 (12)	−0.0086 (12)
C17	0.065 (2)	0.067 (2)	0.073 (2)	0.0022 (18)	−0.0188 (17)	−0.0230 (17)
C18	0.064 (2)	0.106 (3)	0.080 (3)	0.019 (2)	−0.0204 (19)	−0.035 (2)
C19	0.0507 (19)	0.136 (4)	0.0482 (19)	−0.011 (2)	−0.0060 (15)	−0.026 (2)
C20	0.074 (2)	0.098 (3)	0.056 (2)	−0.042 (2)	−0.0102 (18)	−0.0086 (19)
C21	0.069 (2)	0.065 (2)	0.0556 (19)	−0.0159 (17)	−0.0133 (16)	−0.0063 (15)
C22	0.057 (2)	0.232 (7)	0.084 (3)	−0.010 (3)	−0.017 (2)	−0.058 (4)
C23	0.0421 (14)	0.0379 (13)	0.0457 (15)	0.0003 (11)	−0.0125 (11)	−0.0075 (11)
C24	0.0525 (17)	0.0449 (16)	0.0581 (18)	0.0098 (13)	0.0056 (14)	−0.0136 (13)
C25	0.0606 (18)	0.0347 (14)	0.0553 (17)	0.0108 (13)	−0.0033 (14)	−0.0128 (12)
C26	0.0360 (13)	0.0343 (13)	0.0486 (15)	0.0025 (10)	−0.0110 (11)	−0.0093 (11)
C27	0.0389 (14)	0.0419 (14)	0.0550 (16)	0.0079 (12)	−0.0007 (12)	−0.0139 (12)
C28	0.0471 (15)	0.0337 (13)	0.0550 (16)	0.0065 (11)	−0.0063 (12)	−0.0121 (11)
C29	0.0403 (14)	0.0422 (15)	0.0499 (16)	−0.0041 (12)	−0.0003 (12)	−0.0084 (12)
C30	0.067 (2)	0.078 (2)	0.0555 (19)	0.0052 (18)	−0.0188 (16)	−0.0127 (16)

Geometric parameters (Å, º) top

S1—O1	1.425 (3)	C3—H3	0.9300
S1—O2	1.425 (2)	C5—H5	0.9300
S1—N1	1.644 (2)	C6—H6	0.9300
S1—C1	1.759 (3)	C7—H7A	0.9600
S2—O3	1.421 (2)	C7—H7B	0.9600
S2—O4	1.438 (2)	C7—H7C	0.9600
S2—N2	1.647 (2)	C9—H9	0.9300
S2—C11	1.747 (3)	C10—H10	0.9300
S3—O7	1.424 (2)	C12—H12	0.9300
S3—N3	1.641 (2)	C13—H13	0.9300
S3—O6	1.423 (2)	C15—H15C	0.9600
S3—C16	1.758 (3)	C15—H15B	0.9600
S4—O9	1.423 (2)	C15—H15A	0.9600
S4—N4	1.651 (2)	C16—C17	1.390 (5)
S4—O8	1.436 (2)	C16—C21	1.382 (5)
S4—C26	1.751 (3)	C17—C18	1.374 (6)
O5—C14	1.210 (3)	C18—C19	1.378 (7)
O10—C29	1.209 (3)	C19—C20	1.382 (6)
N1—C8	1.416 (4)	C19—C22	1.507 (6)
N2—C14	1.380 (3)	C20—C21	1.381 (6)
N1—H1	0.8600	C23—C28	1.386 (4)
N2—H2A	0.8600	C23—C24	1.392 (3)
N3—C23	1.417 (4)	C24—C25	1.373 (4)
N4—C29	1.381 (3)	C25—C26	1.383 (4)
N3—H3A	0.8600	C26—C27	1.385 (3)
N4—H4	0.8600	C27—C28	1.374 (4)
C1—C6	1.382 (5)	C29—C30	1.492 (5)
C1—C2	1.382 (5)	C17—H17	0.9300
C2—C3	1.391 (6)	C18—H18	0.9300
C3—C4	1.371 (6)	C20—H20	0.9300
C4—C5	1.379 (7)	C21—H21	0.9300
C4—C7	1.505 (6)	C22—H22A	0.9600
C5—C6	1.395 (5)	C22—H22B	0.9600
C8—C13	1.392 (3)	C22—H22C	0.9600
C8—C9	1.382 (4)	C24—H24	0.9300
C9—C10	1.378 (4)	C25—H25	0.9300
C10—C11	1.381 (3)	C27—H27	0.9300
C11—C12	1.387 (4)	C28—H28	0.9300
C12—C13	1.375 (4)	C30—H30A	0.9600
C14—C15	1.490 (5)	C30—H30B	0.9600
C2—H2	0.9300	C30—H30C	0.9600

O1—S1—O2	120.70 (15)	C4—C7—H7B	110.00
O1—S1—N1	104.06 (14)	C4—C7—H7C	110.00
O1—S1—C1	109.20 (17)	C4—C7—H7A	109.00
O2—S1—N1	108.23 (14)	H7B—C7—H7C	109.00
O2—S1—C1	107.86 (15)	C8—C9—H9	120.00
N1—S1—C1	105.84 (14)	C10—C9—H9	120.00
O3—S2—O4	119.35 (12)	C11—C10—H10	120.00
O3—S2—N2	108.69 (12)	C9—C10—H10	120.00
O3—S2—C11	110.10 (13)	C13—C12—H12	120.00
O4—S2—N2	103.10 (12)	C11—C12—H12	120.00
O4—S2—C11	108.62 (12)	C8—C13—H13	120.00
N2—S2—C11	106.04 (12)	C12—C13—H13	120.00
N3—S3—C16	105.24 (14)	C14—C15—H15C	109.00
O7—S3—C16	109.50 (15)	H15B—C15—H15C	110.00
O6—S3—N3	107.70 (13)	C14—C15—H15A	109.00
O6—S3—C16	108.13 (15)	H15A—C15—H15B	110.00
O6—S3—O7	120.60 (14)	H15A—C15—H15C	110.00
O7—S3—N3	104.61 (14)	C14—C15—H15B	109.00
O8—S4—C26	108.63 (12)	S3—C16—C17	119.5 (3)
O9—S4—N4	108.81 (12)	S3—C16—C21	120.2 (3)
O8—S4—N4	102.93 (12)	C17—C16—C21	120.3 (3)
O8—S4—O9	119.59 (12)	C16—C17—C18	119.6 (4)
O9—S4—C26	109.97 (13)	C17—C18—C19	121.3 (4)
N4—S4—C26	105.93 (12)	C18—C19—C22	121.2 (5)
S1—N1—C8	123.5 (2)	C20—C19—C22	120.6 (5)
S2—N2—C14	125.40 (18)	C18—C19—C20	118.2 (4)
C8—N1—H1	118.00	C19—C20—C21	122.0 (4)
S1—N1—H1	118.00	C16—C21—C20	118.6 (4)
S2—N2—H2A	117.00	C24—C23—C28	119.4 (2)
C14—N2—H2A	117.00	N3—C23—C24	121.6 (2)
S3—N3—C23	122.68 (19)	N3—C23—C28	119.0 (2)
S4—N4—C29	125.40 (18)	C23—C24—C25	120.0 (3)
C23—N3—H3A	119.00	C24—C25—C26	119.9 (2)
S3—N3—H3A	119.00	S4—C26—C25	119.41 (19)
C29—N4—H4	117.00	S4—C26—C27	119.8 (2)
S4—N4—H4	117.00	C25—C26—C27	120.7 (2)
C2—C1—C6	120.6 (3)	C26—C27—C28	119.1 (3)
S1—C1—C6	119.6 (3)	C23—C28—C27	120.8 (2)
S1—C1—C2	119.8 (3)	O10—C29—C30	124.3 (3)
C1—C2—C3	118.4 (4)	N4—C29—C30	114.7 (2)
C2—C3—C4	122.2 (4)	O10—C29—N4	121.0 (3)
C3—C4—C5	118.6 (4)	C16—C17—H17	120.00
C5—C4—C7	120.6 (4)	C18—C17—H17	120.00
C3—C4—C7	120.8 (4)	C17—C18—H18	119.00
C4—C5—C6	120.8 (4)	C19—C18—H18	119.00
C1—C6—C5	119.4 (4)	C19—C20—H20	119.00
C9—C8—C13	119.7 (2)	C21—C20—H20	119.00
N1—C8—C13	121.7 (3)	C16—C21—H21	121.00
N1—C8—C9	118.5 (2)	C20—C21—H21	121.00
C8—C9—C10	120.6 (2)	C19—C22—H22A	109.00
C9—C10—C11	119.4 (3)	C19—C22—H22B	110.00
S2—C11—C12	119.58 (19)	C19—C22—H22C	109.00
S2—C11—C10	119.7 (2)	H22A—C22—H22B	109.00
C10—C11—C12	120.6 (2)	H22A—C22—H22C	109.00
C11—C12—C13	119.7 (2)	H22B—C22—H22C	109.00
C8—C13—C12	119.9 (3)	C23—C24—H24	120.00
N2—C14—C15	114.8 (2)	C25—C24—H24	120.00
O5—C14—C15	124.7 (3)	C24—C25—H25	120.00
O5—C14—N2	120.5 (3)	C26—C25—H25	120.00
C1—C2—H2	121.00	C26—C27—H27	120.00
C3—C2—H2	121.00	C28—C27—H27	120.00
C4—C3—H3	119.00	C23—C28—H28	120.00
C2—C3—H3	119.00	C27—C28—H28	120.00
C4—C5—H5	120.00	C29—C30—H30A	109.00
C6—C5—H5	120.00	C29—C30—H30B	109.00
C1—C6—H6	120.00	C29—C30—H30C	109.00
C5—C6—H6	120.00	H30A—C30—H30B	109.00
H7A—C7—H7C	109.00	H30A—C30—H30C	109.00
H7A—C7—H7B	109.00	H30B—C30—H30C	109.00

O1—S1—N1—C8	−173.5 (3)	S4—N4—C29—O10	1.7 (4)
O2—S1—N1—C8	57.0 (3)	S4—N4—C29—C30	−178.4 (2)
C1—S1—N1—C8	−58.4 (3)	C2—C1—C6—C5	−1.6 (4)
O1—S1—C1—C2	−159.9 (2)	S1—C1—C2—C3	−175.9 (3)
O1—S1—C1—C6	22.5 (3)	C6—C1—C2—C3	1.8 (5)
O2—S1—C1—C2	−27.0 (3)	S1—C1—C6—C5	176.1 (2)
O2—S1—C1—C6	155.3 (2)	C1—C2—C3—C4	−0.5 (6)
N1—S1—C1—C2	88.7 (3)	C2—C3—C4—C5	−1.0 (6)
N1—S1—C1—C6	−89.0 (3)	C2—C3—C4—C7	179.5 (4)
O3—S2—N2—C14	48.6 (2)	C7—C4—C5—C6	−179.2 (3)
O4—S2—N2—C14	176.2 (2)	C3—C4—C5—C6	1.3 (5)
C11—S2—N2—C14	−69.7 (2)	C4—C5—C6—C1	0.0 (5)
O3—S2—C11—C10	−27.0 (3)	N1—C8—C13—C12	−179.1 (3)
O3—S2—C11—C12	155.3 (2)	C13—C8—C9—C10	0.8 (4)
O4—S2—C11—C10	−159.3 (2)	N1—C8—C9—C10	177.9 (3)
O4—S2—C11—C12	22.9 (3)	C9—C8—C13—C12	−2.0 (4)
N2—S2—C11—C10	90.4 (3)	C8—C9—C10—C11	1.0 (4)
N2—S2—C11—C12	−87.3 (2)	C9—C10—C11—S2	−179.4 (2)
N3—S3—C16—C17	86.6 (3)	C9—C10—C11—C12	−1.6 (4)
N3—S3—C16—C21	−91.3 (3)	S2—C11—C12—C13	178.2 (2)
O6—S3—N3—C23	−57.2 (3)	C10—C11—C12—C13	0.4 (4)
O7—S3—N3—C23	173.4 (2)	C11—C12—C13—C8	1.4 (4)
C16—S3—N3—C23	58.0 (3)	S3—C16—C17—C18	−175.7 (3)
O6—S3—C16—C17	−158.6 (2)	C21—C16—C17—C18	2.1 (5)
O6—S3—C16—C21	23.6 (3)	S3—C16—C21—C20	176.0 (2)
O7—S3—C16—C17	−25.4 (3)	C17—C16—C21—C20	−1.8 (4)
O7—S3—C16—C21	156.8 (2)	C16—C17—C18—C19	−0.5 (6)
O8—S4—N4—C29	−176.4 (2)	C17—C18—C19—C20	−1.3 (6)
O9—S4—N4—C29	−48.6 (2)	C17—C18—C19—C22	179.1 (4)
C26—S4—N4—C29	69.6 (2)	C18—C19—C20—C21	1.6 (5)
O8—S4—C26—C25	−23.8 (3)	C22—C19—C20—C21	−178.8 (3)
O8—S4—C26—C27	158.2 (2)	C19—C20—C21—C16	0.0 (5)
O9—S4—C26—C25	−156.4 (2)	N3—C23—C24—C25	−180.0 (3)
O9—S4—C26—C27	25.6 (3)	C28—C23—C24—C25	1.7 (4)
N4—S4—C26—C25	86.2 (2)	N3—C23—C28—C27	−179.0 (3)
N4—S4—C26—C27	−91.9 (2)	C24—C23—C28—C27	−0.6 (4)
S1—N1—C8—C9	128.8 (3)	C23—C24—C25—C26	−1.3 (4)
S1—N1—C8—C13	−54.2 (4)	C24—C25—C26—S4	−178.2 (2)
S2—N2—C14—C15	179.5 (2)	C24—C25—C26—C27	−0.2 (4)
S2—N2—C14—O5	−1.4 (4)	S4—C26—C27—C28	179.2 (2)
S3—N3—C23—C28	−127.2 (3)	C25—C26—C27—C28	1.2 (4)
S3—N3—C23—C24	54.5 (4)	C26—C27—C28—C23	−0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.14	2.841 (3)	138
N2—H2A···O4ⁱⁱ	0.86	2.06	2.876 (3)	158
N3—H3A···O10ⁱⁱⁱ	0.86	2.18	2.859 (3)	136
N4—H4···O8^iv	0.86	2.05	2.867 (3)	157
C13—H13···O2	0.93	2.49	3.062 (4)	120
C22—H22A···O6^v	0.96	2.59	3.338 (5)	135
C24—H24···O6	0.93	2.46	3.026 (4)	119

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₅S₂
M_r	368.42
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6722 (3), 11.9968 (4), 15.4784 (6)
α, β, γ (°)	82.802 (2), 79.232 (1), 89.653 (2)
V (Å³)	1750.24 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.35 × 0.25 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.915, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	31011, 8382, 5598
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.153, 1.02
No. of reflections	8382
No. of parameters	438
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.45

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.14	2.841 (3)	138
N2—H2A···O4ⁱⁱ	0.86	2.06	2.876 (3)	158
N3—H3A···O10ⁱⁱⁱ	0.86	2.18	2.859 (3)	136
N4—H4···O8^iv	0.86	2.05	2.867 (3)	157
C13—H13···O2	0.93	2.49	3.062 (4)	120
C22—H22A···O6^v	0.96	2.59	3.338 (5)	135
C24—H24···O6	0.93	2.46	3.026 (4)	119

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

Ashfaq, M., Khan, I. U., Arshad, M. N., Ahmad, H. & Asghar, M. N. (2010). Acta Cryst. E66, o299. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Pages o983-o984

doi:10.1107/S1600536812008616

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A triclinic polymorph of N-[4-(4-methyl­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

A triclinic polymorph of N-[4-(4-methylbenzenesulfonamido)phenylsulfonyl]acetamide