4-Iodo-N-(phenyl­sulfon­yl)benzamide hemihydrate

Suchetan, P.A.; Sudha, A.G.; Suresha, E.; Lokanath, N.K.; Naveen, S.; Warad, I.

doi:10.1107/S2414314617001493

organic compounds

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ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170149

https://doi.org/10.1107/S2414314617001493

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4-Iodo-N-(phenylsulfonyl)benzamide hemihydrate

P. A. Suchetan,^a A. G. Sudha,^a E. Suresha,^a N. K. Lokanath,^b S. Naveen ^c ^* and Ismail Warad ^d ^*

^aDepartment of Chemistry, University College of Science, Tumkur University, Tumkur, 572103, India, ^bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India, ^cInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, and ^dDepartment of Chemistry, Science College, An-Najah National University, PO Box, 7, Nablus, Palestinian Territories
^*Correspondence e-mail: naveen@ioe.uni-mysore.ac.in, khalil.i@najah.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 January 2017; accepted 29 January 2017; online 3 February 2017)

In the title hemihydrate, 2C₁₃H₁₀INO₃S·H₂O, there are two organic molecules (A and B) and one water molecule in the asymmetric unit. The benzene rings are inclined to one another by 77.98 (1)° in A and 79.81 (9)° in B. The A and B molecules are connected through a water molecule via N—H⋯O and O—H⋯O hydrogen bonds. In the extended structure, the A molecules are interlinked via two water molecules through O—H⋯O hydrogen bonds to generate R⁴₄(12) loops. Further, the A and B molecules are linked by N—H⋯O hydrogen bonds, and thus an [010] chain is formed. Several C—H⋯O interactions extend the chains into sheet lying parallel to the ab-plane. The sheets are further extended into a three dimensional architecture via a C—H⋯π interaction.

Keywords: crystal structure; hydrates; sulfonamides; benzamides; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1530045

Structure description

In continuation of our work on the synthesis and crystal structures of N-(phenylsulfonyl)arylamides (Suchetan et al., 2009 , 2010 ; Gowda et al., 2009 ), the title compound was synthesized and we report herein on its crystal structure.

The title hemihydrate (Fig. 1) contains two molecules (A and B) in the asymmetric unit. The benzene rings are inclined to one another by 77.98 (1)° in A and 79.81 (9)° in B. The A and B molecules are interconnected through a water molecule via N1—HN1⋯O7, O7—H1O7⋯O6 and O7—H1O7⋯O5 hydrogen bonds (Table 1). The bifurcated O7—H1O7⋯(O5,O6) hydrogen bonds form R₁²(6) rings (Fig. 1). The A molecules in the neighboring asymmetric units are interlinked via two water molecules through O7—H2O7⋯O1ⁱⁱ (Table 1) hydrogen bonds to form an R₄⁴(12) loop. Further, the A and B molecules in adjacent R₄⁴(12) ring motifs are linked by N2—HN2⋯O2ⁱ (Table 1) hydrogen bonds, and thus, a chain is observed parallel to the b-axis direction (Fig. 2). Further, C9—H9⋯O7, C18—H18⋯O4ⁱⁱⁱ and C26—H26⋯O2ⁱ (Table 1) interactions extend the chains into a sheets in the ab plane (Fig. 3). The sheets are further extended into a three-dimensional architecture via C17—H17⋯π^iv interactions involving the π electrons of the iodobenzene ring of molecule B (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the iodobenzene ring (C21–C26) of molecule B.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯O2ⁱ	0.84	2.12	2.9271	160
N1—HN1⋯O7	0.81	2.01	2.7894	163
O7—H2O7⋯O1ⁱⁱ	0.82	2.09	2.8507	154
O7—H1O7⋯O5	0.83	2.32	2.8283	121
O7—H1O7⋯O6	0.83	2.23	2.9898	152
C9—H9⋯O7	0.95	2.37	3.2680	158
C18—H18⋯O4ⁱⁱⁱ	0.95	2.58	3.429 (5)	149
C26—H26⋯O2ⁱ	0.95	2.59	3.376 (5)	140
C17—H17⋯Cg^iv	0.95	2.88	3.7194	148
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) x-1, y, z.

Figure 1
A view of the molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The N—H⋯O and O—H⋯O hydrogen bonds (dashed lines, see Table 1

) are also shown.

Figure 2
Generation of chains along [010] via several N—H⋯O and O—H⋯O hydrogen bonds (dashed lines, see Table 1

Figure 3
A view along the c axis of the crystal packing of the title compound, showing the N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds (dashed lines; see Table 1

). For clarity, only H atoms involved in hydrogen bonding have been included.

Synthesis and crystallization

The title compound was prepared by refluxing a mixture of 4-iodobenzoic acid (3 mmol), benzenesulfonamide (3 mmol) and phosphorus oxychloride (7 ml) for 3 h on a water bath. The resultant mixture was cooled and poured into ice-cold water. The solid 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 later filtered, dried and recrystallized (m.p. = 460 K). Colourless prisms were obtained by slow evaporation of a solution of the compound in methanol (with a few drops of added water).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	2C₁₃H₁₀INO₃S·H₂O
M_r	792.37
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	10.6311 (5), 11.0403 (5), 12.0340 (6)
α, β, γ (°)	97.594 (2), 92.173 (2), 99.423 (1)
V (Å³)	1378.59 (11)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	19.75
Crystal size (mm)	0.22 × 0.11 × 0.08

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.111, 0.206
No. of measured, independent and observed [I > 2σ(I)] reflections	14470, 4556, 4351
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.585

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.07
No. of reflections	4556
No. of parameters	368
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.23, −1.18
Computer programs: APEX2 and SAINT-Plus (Bruker, 2009), SHELXT2016/4 (Sheldrick, 2015a ), SHELXL2016/4 (Sheldrick, 2015b ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1530045

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001493/hb4117sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001493/hb4117Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001493/hb4117Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT2016/4 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/4 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015b).

4-Iodo-N-(phenylsulfonyl)benzamide hemihydrate top

Crystal data top

2C₁₃H₁₀INO₃S·H₂O	F(000) = 772
M_r = 792.37	Prism
Triclinic, P1	D_x = 1.909 Mg m⁻³
Hall symbol: -P 1	Melting point: 460 K
a = 10.6311 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.0403 (5) Å	Cell parameters from 175 reflections
c = 12.0340 (6) Å	θ = 3.7–64.5°
α = 97.594 (2)°	µ = 19.75 mm⁻¹
β = 92.173 (2)°	T = 173 K
γ = 99.423 (1)°	Prism, colourless
V = 1378.59 (11) Å³	0.22 × 0.11 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	4351 reflections with I > 2σ(I)
Radiation source: CuKα	R_int = 0.052
Graphite monochromator	θ_max = 64.5°, θ_min = 3.7°
phi and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.111, T_max = 0.206	l = −13→12
14470 measured reflections	1 standard reflections every 2 reflections
4556 independent reflections	intensity decay: 0.1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0797P)² + 0.2627P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4556 reflections	Δρ_max = 1.23 e Å⁻³
368 parameters	Δρ_min = −1.18 e Å⁻³
4 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.90191 (2)	0.36213 (2)	−0.13476 (2)	0.02152 (13)
I2	0.23891 (2)	0.22303 (3)	0.99991 (2)	0.02462 (14)
S1	0.36863 (8)	0.18597 (8)	0.38822 (7)	0.0102 (2)
S2	0.77577 (8)	0.20298 (8)	0.46211 (7)	0.0113 (2)
O5	0.7584 (3)	0.2982 (3)	0.3964 (2)	0.0148 (6)
O7	0.5953 (3)	0.4761 (2)	0.3928 (2)	0.0171 (6)
O3	0.4363 (2)	0.0618 (2)	0.1777 (2)	0.0156 (6)
O2	0.3857 (3)	0.0650 (2)	0.4095 (2)	0.0163 (6)
O1	0.3821 (3)	0.2831 (2)	0.4811 (2)	0.0140 (6)
O6	0.6832 (3)	0.4039 (2)	0.6098 (2)	0.0168 (6)
O4	0.7648 (3)	0.0778 (3)	0.4096 (2)	0.0170 (6)
N1	0.4739 (3)	0.2383 (3)	0.3017 (3)	0.0112 (7)
N2	0.6669 (3)	0.1963 (3)	0.5582 (3)	0.0122 (6)
C15	0.9731 (4)	0.3725 (4)	0.5712 (3)	0.0126 (7)
H15	0.926916	0.434422	0.552424	0.015*
C1	0.2180 (3)	0.1746 (3)	0.3169 (3)	0.0125 (7)
C14	0.9236 (4)	0.2471 (3)	0.5399 (3)	0.0116 (7)
C24	0.3720 (4)	0.2426 (4)	0.8768 (3)	0.0164 (8)
C12	0.7210 (4)	0.1779 (4)	−0.0283 (3)	0.0173 (8)
H12	0.743547	0.121332	−0.087657	0.021*
C10	0.7450 (4)	0.3854 (4)	0.0721 (3)	0.0154 (8)
H10	0.784176	0.470125	0.081032	0.019*
C20	0.6363 (3)	0.2989 (3)	0.6239 (3)	0.0120 (7)
C21	0.5443 (3)	0.2734 (3)	0.7113 (3)	0.0115 (7)
C8	0.5987 (4)	0.2195 (4)	0.1336 (3)	0.0124 (8)
C16	1.0901 (4)	0.4050 (4)	0.6297 (3)	0.0151 (8)
H16	1.125122	0.490056	0.651777	0.018*
C7	0.4972 (3)	0.1648 (3)	0.2042 (3)	0.0115 (7)
C19	0.9877 (4)	0.1553 (4)	0.5686 (3)	0.0154 (8)
H19	0.951207	0.070383	0.548274	0.018*
C23	0.4521 (4)	0.3553 (4)	0.8779 (3)	0.0176 (8)
H23	0.448327	0.421848	0.935780	0.021*
C25	0.3778 (4)	0.1433 (4)	0.7931 (3)	0.0148 (8)
H25	0.323712	0.065693	0.792743	0.018*
C11	0.7758 (4)	0.3025 (4)	−0.0153 (3)	0.0155 (8)
C6	0.1536 (4)	0.0613 (4)	0.2665 (3)	0.0186 (8)
H6	0.189454	−0.011585	0.270213	0.022*
C9	0.6569 (4)	0.3438 (4)	0.1463 (3)	0.0152 (8)
H9	0.635821	0.400468	0.206341	0.018*
C22	0.5372 (4)	0.3713 (4)	0.7955 (3)	0.0150 (8)
H22	0.591048	0.449034	0.796067	0.018*
C17	1.1573 (4)	0.3134 (4)	0.6568 (3)	0.0176 (8)
H17	1.239003	0.336432	0.695619	0.021*
C2	0.1678 (4)	0.2839 (4)	0.3122 (3)	0.0194 (8)
H2	0.213500	0.361512	0.347460	0.023*
C26	0.4635 (4)	0.1603 (4)	0.7114 (3)	0.0137 (8)
H26	0.467745	0.093534	0.653865	0.016*
C18	1.1058 (4)	0.1885 (4)	0.6273 (4)	0.0192 (9)
H18	1.151187	0.126474	0.647265	0.023*
C13	0.6336 (4)	0.1376 (4)	0.0459 (3)	0.0162 (8)
H13	0.596126	0.052405	0.037462	0.019*
C4	−0.0152 (4)	0.1618 (5)	0.2050 (4)	0.0301 (11)
H4	−0.095970	0.157034	0.166620	0.036*
C3	0.0513 (5)	0.2767 (5)	0.2559 (4)	0.0297 (11)
H3	0.016110	0.349761	0.251479	0.036*
C5	0.0360 (4)	0.0544 (5)	0.2103 (4)	0.0287 (10)
H5	−0.009541	−0.023486	0.175348	0.034*
H2O7	0.578 (6)	0.543 (3)	0.420 (5)	0.040 (16)*
H1O7	0.643 (4)	0.457 (5)	0.441 (4)	0.026 (14)*
HN2	0.637 (4)	0.127 (3)	0.577 (4)	0.017 (11)*
HN1	0.507 (5)	0.310 (3)	0.315 (5)	0.030 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01479 (19)	0.0317 (2)	0.0166 (2)	−0.00216 (12)	0.00650 (12)	0.00403 (13)
I2	0.0180 (2)	0.0412 (2)	0.0176 (2)	0.00979 (14)	0.00791 (13)	0.00722 (14)
S1	0.0087 (4)	0.0085 (4)	0.0127 (5)	−0.0003 (3)	0.0025 (3)	0.0011 (3)
S2	0.0082 (4)	0.0102 (4)	0.0149 (5)	−0.0008 (3)	0.0027 (3)	0.0013 (3)
O5	0.0111 (13)	0.0200 (14)	0.0142 (14)	0.0009 (10)	0.0017 (10)	0.0072 (11)
O7	0.0195 (15)	0.0094 (14)	0.0214 (15)	0.0017 (11)	0.0022 (12)	−0.0003 (11)
O3	0.0157 (13)	0.0102 (13)	0.0189 (14)	−0.0015 (10)	0.0041 (11)	−0.0020 (10)
O2	0.0188 (14)	0.0127 (13)	0.0193 (14)	0.0051 (10)	0.0038 (11)	0.0053 (11)
O1	0.0148 (14)	0.0138 (13)	0.0116 (14)	−0.0010 (10)	0.0021 (11)	−0.0011 (10)
O6	0.0174 (14)	0.0099 (14)	0.0212 (15)	−0.0022 (10)	0.0016 (11)	0.0013 (11)
O4	0.0148 (14)	0.0160 (14)	0.0175 (14)	−0.0010 (10)	0.0057 (11)	−0.0047 (11)
N1	0.0099 (16)	0.0115 (17)	0.0101 (16)	−0.0021 (12)	0.0021 (12)	−0.0012 (13)
N2	0.0104 (15)	0.0081 (16)	0.0185 (17)	0.0000 (12)	0.0048 (12)	0.0043 (13)
C15	0.0119 (18)	0.0126 (19)	0.0138 (19)	0.0015 (14)	0.0044 (14)	0.0035 (15)
C1	0.0090 (18)	0.0163 (19)	0.0113 (18)	−0.0009 (14)	0.0050 (14)	0.0012 (14)
C14	0.0087 (18)	0.0136 (18)	0.0112 (18)	−0.0016 (14)	0.0029 (14)	0.0014 (15)
C24	0.014 (2)	0.027 (2)	0.012 (2)	0.0100 (16)	−0.0006 (15)	0.0041 (16)
C12	0.016 (2)	0.020 (2)	0.0141 (19)	0.0016 (16)	0.0046 (15)	−0.0032 (16)
C10	0.015 (2)	0.016 (2)	0.014 (2)	−0.0032 (15)	0.0059 (15)	0.0028 (15)
C20	0.0074 (17)	0.0136 (19)	0.0149 (19)	0.0012 (14)	−0.0026 (14)	0.0033 (14)
C21	0.0065 (17)	0.0140 (18)	0.0140 (19)	0.0022 (14)	−0.0023 (14)	0.0019 (14)
C8	0.0099 (18)	0.0134 (18)	0.0136 (19)	0.0026 (14)	−0.0015 (14)	0.0004 (15)
C16	0.0136 (19)	0.0151 (19)	0.016 (2)	−0.0016 (15)	0.0029 (15)	0.0044 (15)
C7	0.0085 (17)	0.0123 (19)	0.0131 (19)	0.0029 (14)	−0.0016 (14)	−0.0010 (15)
C19	0.0120 (19)	0.0122 (18)	0.022 (2)	0.0012 (14)	0.0077 (15)	0.0030 (15)
C23	0.016 (2)	0.021 (2)	0.014 (2)	0.0039 (15)	−0.0012 (15)	−0.0030 (15)
C25	0.0134 (19)	0.0140 (19)	0.018 (2)	0.0022 (15)	0.0025 (15)	0.0066 (15)
C11	0.0116 (18)	0.022 (2)	0.0141 (19)	0.0011 (15)	0.0025 (15)	0.0065 (16)
C6	0.015 (2)	0.021 (2)	0.017 (2)	−0.0025 (15)	0.0013 (15)	0.0016 (16)
C9	0.0150 (19)	0.016 (2)	0.0139 (19)	0.0038 (15)	0.0050 (15)	−0.0016 (15)
C22	0.0132 (19)	0.0127 (19)	0.017 (2)	0.0001 (14)	−0.0033 (15)	−0.0005 (15)
C17	0.0081 (18)	0.027 (2)	0.019 (2)	0.0012 (15)	0.0022 (15)	0.0079 (16)
C2	0.019 (2)	0.021 (2)	0.020 (2)	0.0065 (16)	0.0074 (16)	0.0053 (17)
C26	0.0114 (18)	0.0141 (19)	0.016 (2)	0.0041 (14)	0.0030 (15)	0.0016 (15)
C18	0.013 (2)	0.022 (2)	0.024 (2)	0.0056 (16)	0.0046 (16)	0.0071 (17)
C13	0.0110 (18)	0.018 (2)	0.017 (2)	−0.0016 (14)	0.0012 (15)	−0.0022 (15)
C4	0.013 (2)	0.053 (3)	0.023 (2)	0.001 (2)	0.0009 (17)	0.009 (2)
C3	0.023 (2)	0.037 (3)	0.035 (3)	0.014 (2)	0.003 (2)	0.013 (2)
C5	0.017 (2)	0.040 (3)	0.024 (2)	−0.0112 (19)	−0.0010 (18)	0.0030 (19)

Geometric parameters (Å, º) top

I1—C11	2.099 (4)	C10—H10	0.9500
I2—C24	2.094 (4)	C20—C21	1.485 (6)
S1—O1	1.428 (3)	C21—C22	1.395 (6)
S1—O2	1.432 (3)	C21—C26	1.396 (6)
S1—N1	1.645 (3)	C8—C9	1.396 (6)
S1—C1	1.766 (4)	C8—C13	1.399 (6)
S2—O4	1.426 (3)	C8—C7	1.497 (6)
S2—O5	1.427 (3)	C16—C17	1.396 (6)
S2—N2	1.666 (3)	C16—H16	0.9500
S2—C14	1.761 (4)	C19—C18	1.388 (6)
O7—H2O7	0.82 (2)	C19—H19	0.9500
O7—H1O7	0.83 (2)	C23—C22	1.376 (6)
O3—C7	1.210 (5)	C23—H23	0.9500
O6—C20	1.220 (5)	C25—C26	1.376 (6)
N1—C7	1.390 (5)	C25—H25	0.9500
N1—HN1	0.81 (3)	C6—C5	1.385 (6)
N2—C20	1.386 (5)	C6—H6	0.9500
N2—HN2	0.84 (3)	C9—H9	0.9500
C15—C16	1.375 (6)	C22—H22	0.9500
C15—C14	1.394 (5)	C17—C18	1.391 (6)
C15—H15	0.9500	C17—H17	0.9500
C1—C6	1.375 (6)	C2—C3	1.375 (7)
C1—C2	1.404 (6)	C2—H2	0.9500
C14—C19	1.383 (5)	C26—H26	0.9500
C24—C23	1.387 (6)	C18—H18	0.9500
C24—C25	1.398 (6)	C13—H13	0.9500
C12—C13	1.376 (6)	C4—C5	1.392 (7)
C12—C11	1.389 (6)	C4—C3	1.397 (7)
C12—H12	0.9500	C4—H4	0.9500
C10—C9	1.384 (6)	C3—H3	0.9500
C10—C11	1.385 (6)	C5—H5	0.9500

O1—S1—O2	118.27 (17)	O3—C7—N1	120.8 (3)
O1—S1—N1	104.13 (17)	O3—C7—C8	122.0 (3)
O2—S1—N1	110.25 (17)	N1—C7—C8	117.2 (3)
O1—S1—C1	109.10 (17)	C14—C19—C18	119.3 (4)
O2—S1—C1	108.84 (17)	C14—C19—H19	120.3
N1—S1—C1	105.46 (17)	C18—C19—H19	120.3
O4—S2—O5	120.03 (17)	C22—C23—C24	120.3 (4)
O4—S2—N2	103.98 (16)	C22—C23—H23	119.9
O5—S2—N2	109.06 (16)	C24—C23—H23	119.9
O4—S2—C14	109.29 (17)	C26—C25—C24	118.7 (4)
O5—S2—C14	108.55 (17)	C26—C25—H25	120.7
N2—S2—C14	104.88 (17)	C24—C25—H25	120.7
H2O7—O7—H1O7	105 (6)	C10—C11—C12	120.9 (4)
C7—N1—S1	121.4 (3)	C10—C11—I1	121.1 (3)
C7—N1—HN1	121 (4)	C12—C11—I1	118.0 (3)
S1—N1—HN1	117 (4)	C1—C6—C5	119.3 (4)
C20—N2—S2	124.3 (3)	C1—C6—H6	120.3
C20—N2—HN2	116 (3)	C5—C6—H6	120.3
S2—N2—HN2	119 (3)	C10—C9—C8	120.6 (4)
C16—C15—C14	118.9 (4)	C10—C9—H9	119.7
C16—C15—H15	120.6	C8—C9—H9	119.7
C14—C15—H15	120.6	C23—C22—C21	120.1 (4)
C6—C1—C2	121.6 (4)	C23—C22—H22	120.0
C6—C1—S1	120.2 (3)	C21—C22—H22	120.0
C2—C1—S1	118.3 (3)	C18—C17—C16	120.6 (4)
C19—C14—C15	121.6 (4)	C18—C17—H17	119.7
C19—C14—S2	118.6 (3)	C16—C17—H17	119.7
C15—C14—S2	119.8 (3)	C3—C2—C1	118.9 (4)
C23—C24—C25	120.5 (4)	C3—C2—H2	120.5
C23—C24—I2	119.4 (3)	C1—C2—H2	120.5
C25—C24—I2	120.0 (3)	C25—C26—C21	121.4 (4)
C13—C12—C11	119.1 (4)	C25—C26—H26	119.3
C13—C12—H12	120.4	C21—C26—H26	119.3
C11—C12—H12	120.4	C19—C18—C17	119.5 (4)
C9—C10—C11	119.5 (4)	C19—C18—H18	120.3
C9—C10—H10	120.2	C17—C18—H18	120.3
C11—C10—H10	120.2	C12—C13—C8	121.3 (4)
O6—C20—N2	121.1 (3)	C12—C13—H13	119.3
O6—C20—C21	122.6 (3)	C8—C13—H13	119.3
N2—C20—C21	116.3 (3)	C5—C4—C3	120.5 (4)
C22—C21—C26	119.1 (4)	C5—C4—H4	119.8
C22—C21—C20	116.8 (3)	C3—C4—H4	119.8
C26—C21—C20	124.1 (3)	C2—C3—C4	119.9 (4)
C9—C8—C13	118.5 (4)	C2—C3—H3	120.0
C9—C8—C7	125.7 (3)	C4—C3—H3	120.0
C13—C8—C7	115.8 (3)	C6—C5—C4	119.8 (4)
C15—C16—C17	120.1 (4)	C6—C5—H5	120.1
C15—C16—H16	119.9	C4—C5—H5	120.1
C17—C16—H16	119.9

O1—S1—N1—C7	174.5 (3)	C15—C14—C19—C18	−1.7 (6)
O2—S1—N1—C7	46.7 (3)	S2—C14—C19—C18	178.3 (3)
C1—S1—N1—C7	−70.6 (3)	C25—C24—C23—C22	1.0 (6)
O4—S2—N2—C20	−174.6 (3)	I2—C24—C23—C22	−177.8 (3)
O5—S2—N2—C20	−45.4 (3)	C23—C24—C25—C26	−0.7 (6)
C14—S2—N2—C20	70.7 (3)	I2—C24—C25—C26	178.0 (3)
O1—S1—C1—C6	−146.8 (3)	C9—C10—C11—C12	−1.1 (6)
O2—S1—C1—C6	−16.4 (4)	C9—C10—C11—I1	176.9 (3)
N1—S1—C1—C6	101.9 (3)	C13—C12—C11—C10	1.0 (6)
O1—S1—C1—C2	34.0 (4)	C13—C12—C11—I1	−177.1 (3)
O2—S1—C1—C2	164.4 (3)	C2—C1—C6—C5	−0.4 (6)
N1—S1—C1—C2	−77.3 (3)	S1—C1—C6—C5	−179.5 (3)
C16—C15—C14—C19	1.5 (6)	C11—C10—C9—C8	−0.2 (6)
C16—C15—C14—S2	−178.5 (3)	C13—C8—C9—C10	1.4 (6)
O4—S2—C14—C19	−18.8 (3)	C7—C8—C9—C10	−176.6 (4)
O5—S2—C14—C19	−151.4 (3)	C24—C23—C22—C21	−0.9 (6)
N2—S2—C14—C19	92.1 (3)	C26—C21—C22—C23	0.6 (5)
O4—S2—C14—C15	161.2 (3)	C20—C21—C22—C23	178.6 (3)
O5—S2—C14—C15	28.6 (4)	C15—C16—C17—C18	−1.5 (6)
N2—S2—C14—C15	−87.8 (3)	C6—C1—C2—C3	0.1 (6)
S2—N2—C20—O6	4.8 (5)	S1—C1—C2—C3	179.2 (3)
S2—N2—C20—C21	−175.2 (2)	C24—C25—C26—C21	0.5 (6)
O6—C20—C21—C22	−15.9 (5)	C22—C21—C26—C25	−0.4 (5)
N2—C20—C21—C22	164.2 (3)	C20—C21—C26—C25	−178.3 (3)
O6—C20—C21—C26	162.1 (3)	C14—C19—C18—C17	0.3 (6)
N2—C20—C21—C26	−17.9 (5)	C16—C17—C18—C19	1.3 (6)
C14—C15—C16—C17	0.1 (6)	C11—C12—C13—C8	0.3 (6)
S1—N1—C7—O3	3.4 (5)	C9—C8—C13—C12	−1.5 (6)
S1—N1—C7—C8	−177.6 (3)	C7—C8—C13—C12	176.7 (3)
C9—C8—C7—O3	167.6 (4)	C1—C2—C3—C4	0.4 (7)
C13—C8—C7—O3	−10.4 (5)	C5—C4—C3—C2	−0.5 (7)
C9—C8—C7—N1	−11.4 (5)	C1—C6—C5—C4	0.3 (6)
C13—C8—C7—N1	170.6 (3)	C3—C4—C5—C6	0.2 (7)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the iodobenzene ring (C21–C26) of molecule B.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O2ⁱ	0.84	2.12	2.9271	160
N1—HN1···O7	0.81	2.01	2.7894	163
O7—H2O7···O1ⁱⁱ	0.82	2.09	2.8507	154
O7—H1O7···O5	0.83	2.32	2.8283	121
O7—H1O7···O6	0.83	2.23	2.9898	152
C9—H9···O7	0.95	2.37	3.2680	158
C18—H18···O4ⁱⁱⁱ	0.95	2.58	3.429 (5)	149
C26—H26···O2ⁱ	0.95	2.59	3.376 (5)	140
C17—H17···Cg^iv	0.95	2.88	3.7194	148

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

Acknowledgements

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data.

References

Bruker (2009). APEX2, SADABS and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156. Web of Science CSD CrossRef IUCr Journals Google Scholar
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1772. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 2| Part 2| February 2017| x170149

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

4-Iodo-N-(phenyl­sulfon­yl)benzamide hemihydrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

4-Iodo-N-(phenylsulfonyl)benzamide hemihydrate