4-[(Z)-(2-Eth­oxy-4-oxochroman-3-yl­idene)methyl­amino]benzene­sulfonamide monohydrate

Mariya-al-Rashida; Tahir, M.N.; Nagra, S.A.; Imran, M.; Iqbal, J.

doi:10.1107/S1600536809026154

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1818-o1819

doi:10.1107/S1600536809026154

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4-[(Z)-(2-Ethoxy-4-oxochroman-3-ylidene)methylamino]benzenesulfonamide monohydrate

Mariya-al-Rashida,^a M. Nawaz Tahir,^b ^* Saeed Ahmad Nagra,^a Muhammed Imran ^a and Javed Iqbal ^a

^aInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 July 2009; accepted 5 July 2009; online 11 July 2009)

In the molecule of the title compound, C₁₈H₁₈N₂O₅S·H₂O, the heterocyclic ring adopts a twisted conformation, while the aromatic rings are oriented at a dihedral angle of 45.46 (3)°. Intramolecular C—H⋯O and N—H⋯O interactions result in the formations of planar five- and six-membered rings. In the crystal structure, N—H⋯O hydrogen bonds link the NH₂ and SO₂ groups through R₂²(8) ring motifs, while C—H⋯O and N—H⋯O hydrogen bonds result in the formation of R₂¹(7) ring motifs. N—H⋯O and O—H⋯O hydrogen bonds link the uncoordinated water molecules, forming a polymeric network. A weak C—H⋯π interaction is also present.

Related literature

For related structures, see: Al-Zaydi et al. (2007 ); Chohan et al. (2008 , 2009 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For ring motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₅S·H₂O
M_r = 392.42
Triclinic, $[P \overline 1]$
a = 8.2727 (6) Å
b = 10.0166 (8) Å
c = 11.5830 (9) Å
α = 102.480 (5)°
β = 97.049 (4)°
γ = 96.731 (4)°
V = 919.77 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.28 × 0.10 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.973, T_max = 0.982
18417 measured reflections
4729 independent reflections
2022 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.125
S = 1.00
4729 reflections
260 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.04	2.696 (3)	132
N2—H21⋯O6ⁱ	0.91 (3)	1.94 (3)	2.838 (4)	169 (3)
N2—H22⋯O2ⁱⁱ	0.85 (3)	2.22 (3)	3.027 (3)	159 (3)
O6—H61⋯O5	0.90 (4)	2.10 (4)	2.999 (3)	176.7 (16)
O6—H62⋯O4ⁱⁱⁱ	0.92 (3)	1.90 (3)	2.784 (3)	161 (3)
C2—H2⋯O2^iv	0.93	2.42	3.300 (4)	157
C9—H9⋯O1^v	1.04 (3)	2.54 (3)	3.472 (3)	149 (2)
C13—H13⋯O2ⁱⁱ	0.93	2.54	3.418 (3)	158
C15—H15⋯O1	0.93	2.50	2.884 (3)	105
C16—H16⋯Cg1^vi	0.93	2.95	3.565 (3)	125
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z-1; (iii) -x, -y+1, -z; (iv) -x, -y, -z; (v) -x+1, -y, -z; (vi) x+1, y, z. Cg1 is the centroid of the C1–C6 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809026154/hk2734sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026154/hk2734Isup2.hkl

checkCIF report

Comment top

Sulfonamides have wide range of applications in medicinal chemistry. Keeping in wiew the importance of sulfonamide derivatives, we have synthesized the title compound, (I). We report herein its crystal structure.

The crystal structures of 4-[(E)-(5-chloro-2-hydroxybenzylidene)amino] benzenesulfonamide, (II) (Chohan et al., 2009) and 4-{2-[(5-chloro-2 -hydroxybenzylidene)amino]ethyl}benzenesulfonamide, (III) (Chohan et al., 2008) have been published, which contain the benzenesulfonamide. The crystal structure of 3-(4-chlorophenylhydrazono)-2-ethoxychroman-4-one, (IV) (Al-Zaydi et al., 2007) has also been published, which contains the common moiety of (I) other than benzenesulfonamide.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring B (O3/C1/C6-C9) is not planar, having total puckering amplitude, Q_T, of 0.444 (3) Å and twisted conformation [ϕ = 84.93 (3) and θ = 70.07 (3) °] (Cremer & Pople, 1975). Rings A (C1-C6) and C (C11-C16) are, of course, planar, and they are oriented at a dihedral angle of A/C = 45.46 (3)°. Intramolecular C-H···O and N-H···O interactions (Table 1) result in the formations of planar five- and six-membered rings D (S1/O1/C14/C15/H15) and E (O4/N1/C7/C8/C10/H1).

In the crystal structure, N-H···O hydrogen bonds link the NH₂ and SO₂ groups through R₂²(8) ring motifs, while C-H···O and N-H···O hydrogen bonds (Table 1) result in the formations of R₂¹(7) ring motifs (Bernstein et al., 1995). On the other hand, N-H···O and O-H···O hydrogen bonds (Table 1) link the lattice water molecules to form a polymeric network (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction.

Related literature top

For related structures, see: Al-Zaydi et al. (2007); Chohan et al. (2008); Chohan et al. (2009). For ring puckering parameters, see: Cremer & Pople (1975). For ring motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the C1–C6 ring.

Experimental top

3-Formylchromone (0.174 g, 1 mmol) in ethanol (5-7 ml) was stirred with heating until dissolved, then catalytic amount of p-toluenesulfonic acid was added, followed by 4-aminobenzenesulfonamide (0.172 g, 1 mmol) in equal amount of ethanol. Reaction mixture was refluxed with stirring for 4 h. The clear yellow solution was kept overnight and solvent was evaporated to yield bright yellow crystalline solid. Product was recrystallized from a mixture of ethanol and acetone (1:1) to yield fine transparent yellow needles.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-[(Z)-(2-Ethoxy-4-oxochroman-3-ylidene)methylamino]benzenesulfonamide monohydrate top

Crystal data top

C₁₈H₁₈N₂O₅S·H₂O	Z = 2
M_r = 392.42	F(000) = 412
Triclinic, P1	D_x = 1.417 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2727 (6) Å	Cell parameters from 4729 reflections
b = 10.0166 (8) Å	θ = 2.4–28.8°
c = 11.5830 (9) Å	µ = 0.21 mm⁻¹
α = 102.480 (5)°	T = 296 K
β = 97.049 (4)°	Needle, yellow
γ = 96.731 (4)°	0.28 × 0.10 × 0.09 mm
V = 919.77 (12) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4729 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.8°, θ_min = 2.4°
ω scans	h = −11→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.973, T_max = 0.982	l = −15→15
18417 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0427P)²] where P = (F_o² + 2F_c²)/3
4729 reflections	(Δ/σ)_max < 0.001
260 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₅S·H₂O	γ = 96.731 (4)°
M_r = 392.42	V = 919.77 (12) Å³
Triclinic, P1	Z = 2
a = 8.2727 (6) Å	Mo Kα radiation
b = 10.0166 (8) Å	µ = 0.21 mm⁻¹
c = 11.5830 (9) Å	T = 296 K
α = 102.480 (5)°	0.28 × 0.10 × 0.09 mm
β = 97.049 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4729 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2022 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.070
18417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.25 e Å⁻³
4729 reflections	Δρ_min = −0.22 e Å⁻³
260 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	0.65357 (9)	0.03978 (8)	−0.32059 (7)	0.0444 (3)
O1	0.7917 (2)	0.0360 (2)	−0.23543 (17)	0.0608 (8)
O2	0.5862 (2)	−0.08348 (18)	−0.41008 (16)	0.0501 (7)
O3	−0.2219 (2)	0.19797 (19)	0.24854 (17)	0.0513 (7)
O4	−0.1312 (2)	0.3631 (2)	−0.03129 (17)	0.0580 (8)
O5	0.0431 (2)	0.3149 (2)	0.31661 (16)	0.0510 (7)
O6	0.1102 (3)	0.5917 (2)	0.2582 (2)	0.0705 (9)
N1	0.1144 (3)	0.2091 (2)	−0.0546 (2)	0.0478 (9)
N2	0.7070 (3)	0.1526 (3)	−0.3923 (3)	0.0559 (10)
C1	−0.3062 (3)	0.3009 (3)	0.2233 (3)	0.0412 (10)
C2	−0.4381 (3)	0.3273 (3)	0.2838 (3)	0.0558 (11)
C3	−0.5269 (4)	0.4275 (3)	0.2598 (3)	0.0628 (11)
C4	−0.4871 (4)	0.5029 (3)	0.1782 (3)	0.0588 (12)
C5	−0.3605 (3)	0.4734 (3)	0.1166 (3)	0.0491 (11)
C6	−0.2684 (3)	0.3703 (3)	0.1377 (2)	0.0376 (9)
C7	−0.1412 (3)	0.3271 (3)	0.0643 (2)	0.0403 (9)
C8	−0.0367 (3)	0.2398 (3)	0.1090 (2)	0.0405 (9)
C9	−0.0540 (3)	0.2094 (3)	0.2276 (3)	0.0470 (11)
C10	0.0843 (3)	0.1890 (3)	0.0508 (3)	0.0469 (11)
C11	0.2442 (3)	0.1665 (3)	−0.1153 (3)	0.0424 (10)
C12	0.2237 (3)	0.1498 (3)	−0.2378 (3)	0.0479 (11)
C13	0.3481 (3)	0.1123 (3)	−0.3005 (2)	0.0463 (10)
C14	0.4946 (3)	0.0904 (3)	−0.2408 (2)	0.0392 (9)
C15	0.5153 (3)	0.1090 (3)	−0.1186 (3)	0.0455 (10)
C16	0.3895 (3)	0.1473 (3)	−0.0555 (2)	0.0471 (10)
C17	0.0555 (4)	0.2828 (4)	0.4337 (3)	0.0756 (16)
C18	0.1854 (4)	0.3812 (4)	0.5152 (3)	0.0916 (16)
H1	0.04755	0.25264	−0.08969	0.0574*
H2	−0.46546	0.27765	0.33962	0.0668*
H3	−0.61609	0.44513	0.29940	0.0754*
H4	−0.54606	0.57326	0.16535	0.0707*
H5	−0.33511	0.52237	0.05987	0.0590*
H9	−0.013 (3)	0.120 (3)	0.243 (2)	0.0563*
H10	0.15063	0.13653	0.08753	0.0562*
H12	0.12514	0.16395	−0.27815	0.0573*
H13	0.33404	0.10157	−0.38301	0.0557*
H15	0.61413	0.09592	−0.07795	0.0545*
H16	0.40398	0.15997	0.02722	0.0565*
H17A	0.08048	0.18955	0.42767	0.0909*
H17B	−0.04851	0.28840	0.46382	0.0909*
H18A	0.16603	0.47367	0.51433	0.1377*
H18B	0.28992	0.36745	0.49030	0.1377*
H18C	0.18604	0.36752	0.59477	0.1377*
H21	0.757 (3)	0.234 (3)	−0.342 (3)	0.0671*
H22	0.634 (4)	0.155 (3)	−0.450 (3)	0.0671*
H61	0.086 (4)	0.508 (4)	0.274 (3)	0.0846*
H62	0.110 (4)	0.586 (3)	0.178 (3)	0.0846*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0396 (4)	0.0481 (5)	0.0453 (5)	0.0093 (3)	0.0075 (3)	0.0083 (4)
O1	0.0433 (11)	0.0813 (16)	0.0562 (14)	0.0244 (10)	0.0001 (10)	0.0088 (11)
O2	0.0598 (12)	0.0394 (12)	0.0470 (12)	0.0060 (10)	0.0096 (10)	0.0015 (10)
O3	0.0436 (11)	0.0510 (13)	0.0676 (14)	0.0071 (10)	0.0156 (10)	0.0278 (11)
O4	0.0622 (13)	0.0742 (15)	0.0450 (13)	0.0114 (11)	0.0120 (10)	0.0273 (12)
O5	0.0523 (12)	0.0600 (14)	0.0410 (12)	0.0048 (10)	0.0064 (10)	0.0149 (11)
O6	0.0939 (17)	0.0584 (15)	0.0519 (14)	−0.0130 (13)	0.0058 (13)	0.0132 (13)
N1	0.0435 (14)	0.0551 (16)	0.0440 (15)	0.0087 (12)	0.0052 (12)	0.0098 (13)
N2	0.0537 (17)	0.0521 (17)	0.0577 (19)	−0.0052 (14)	0.0098 (13)	0.0099 (15)
C1	0.0357 (15)	0.0402 (17)	0.0482 (18)	0.0026 (14)	0.0053 (14)	0.0140 (15)
C2	0.0441 (18)	0.069 (2)	0.063 (2)	0.0092 (17)	0.0175 (16)	0.0283 (18)
C3	0.0491 (19)	0.079 (2)	0.067 (2)	0.0201 (19)	0.0192 (17)	0.020 (2)
C4	0.061 (2)	0.058 (2)	0.060 (2)	0.0250 (17)	0.0078 (18)	0.0118 (18)
C5	0.0515 (18)	0.0467 (19)	0.0511 (19)	0.0082 (16)	0.0034 (16)	0.0176 (16)
C6	0.0356 (15)	0.0384 (16)	0.0357 (16)	−0.0013 (13)	0.0018 (13)	0.0079 (14)
C7	0.0411 (16)	0.0420 (17)	0.0328 (16)	−0.0036 (14)	0.0037 (14)	0.0045 (14)
C8	0.0365 (15)	0.0442 (17)	0.0399 (17)	0.0053 (14)	0.0063 (14)	0.0079 (14)
C9	0.0425 (17)	0.052 (2)	0.050 (2)	0.0096 (16)	0.0121 (15)	0.0154 (17)
C10	0.0437 (17)	0.0494 (19)	0.0453 (19)	0.0031 (15)	0.0011 (15)	0.0114 (15)
C11	0.0353 (16)	0.0406 (17)	0.0481 (19)	0.0032 (14)	0.0076 (15)	0.0043 (14)
C12	0.0400 (16)	0.059 (2)	0.0435 (19)	0.0105 (15)	−0.0002 (15)	0.0115 (16)
C13	0.0452 (17)	0.059 (2)	0.0350 (16)	0.0122 (15)	0.0045 (14)	0.0102 (15)
C14	0.0375 (15)	0.0382 (16)	0.0401 (17)	0.0032 (13)	0.0050 (13)	0.0073 (14)
C15	0.0420 (16)	0.0506 (19)	0.0392 (18)	0.0047 (14)	−0.0021 (14)	0.0065 (15)
C16	0.0441 (17)	0.062 (2)	0.0294 (15)	0.0028 (15)	0.0008 (14)	0.0035 (14)
C17	0.087 (3)	0.094 (3)	0.053 (2)	0.018 (2)	0.015 (2)	0.028 (2)
C18	0.099 (3)	0.116 (3)	0.051 (2)	0.013 (3)	−0.010 (2)	0.014 (2)

Geometric parameters (Å, º) top

S1—O1	1.425 (2)	C8—C10	1.361 (4)
S1—O2	1.433 (2)	C8—C9	1.490 (4)
S1—N2	1.594 (3)	C11—C16	1.367 (4)
S1—C14	1.759 (3)	C11—C12	1.379 (5)
O3—C1	1.372 (3)	C12—C13	1.373 (4)
O3—C9	1.435 (3)	C13—C14	1.385 (4)
O4—C7	1.245 (3)	C14—C15	1.374 (4)
O5—C9	1.397 (4)	C15—C16	1.387 (4)
O5—C17	1.454 (4)	C17—C18	1.455 (5)
O6—H62	0.92 (3)	C2—H2	0.9300
O6—H61	0.90 (4)	C3—H3	0.9300
N1—C11	1.412 (4)	C4—H4	0.9300
N1—C10	1.327 (4)	C5—H5	0.9300
N1—H1	0.8600	C9—H9	1.04 (3)
N2—H21	0.91 (3)	C10—H10	0.9300
N2—H22	0.85 (3)	C12—H12	0.9300
C1—C6	1.374 (4)	C13—H13	0.9300
C1—C2	1.388 (4)	C15—H15	0.9300
C2—C3	1.367 (4)	C16—H16	0.9300
C3—C4	1.378 (5)	C17—H17B	0.9700
C4—C5	1.363 (4)	C17—H17A	0.9700
C5—C6	1.398 (4)	C18—H18C	0.9600
C6—C7	1.478 (3)	C18—H18A	0.9600
C7—C8	1.429 (4)	C18—H18B	0.9600

O1···N1ⁱ	3.239 (3)	C7···H1	2.5600
O2···C13ⁱⁱ	3.418 (3)	C7···H61	2.98 (4)
O2···N2ⁱⁱ	3.027 (3)	C7···H62	3.06 (3)
O2···C2ⁱⁱⁱ	3.300 (4)	C8···H61	2.93 (4)
O3···C13ⁱⁱⁱ	3.364 (4)	C9···H61	2.99 (4)
O4···O4^iv	3.181 (3)	C10···H16	2.7300
O4···O6^iv	2.784 (3)	C11···H5^iv	3.0300
O4···N1	2.696 (3)	C12···H9ⁱⁱⁱ	3.02 (3)
O5···C6	3.281 (3)	C16···H10	2.7400
O5···O6	2.999 (3)	H1···O4	2.0400
O6···C7	3.374 (3)	H1···O1^vii	2.9200
O6···O5	2.999 (3)	H1···C7	2.5600
O6···N2^v	2.838 (4)	H1···H12	2.3700
O6···O4^iv	2.784 (3)	H1···H62^iv	2.5000
O1···H15	2.5000	H2···O2ⁱⁱⁱ	2.4200
O1···H9^vi	2.54 (3)	H3···O6^vii	2.8900
O1···H1ⁱ	2.9200	H4···H5^ix	2.6000
O1···H10^vi	2.7200	H5···C5^ix	3.0500
O2···H22ⁱⁱ	2.22 (3)	H5···C4^ix	2.9100
O2···H13ⁱⁱ	2.5400	H5···O4	2.6200
O2···H2ⁱⁱⁱ	2.4200	H5···C11^iv	3.0300
O3···H17B	2.6300	H5···H4^ix	2.6000
O4···H5	2.6200	H9···H10	2.4000
O4···H62^iv	1.90 (3)	H9···C12ⁱⁱⁱ	3.02 (3)
O4···H1	2.0400	H9···H17A	2.1200
O5···H61	2.10 (4)	H9···O1^vi	2.54 (3)
O6···H3ⁱ	2.8900	H10···C16	2.7400
O6···H21^v	1.94 (3)	H10···H16	2.2900
N1···O1^vii	3.239 (3)	H10···O1^vi	2.7200
N1···O4	2.696 (3)	H10···H9	2.4000
N2···O6^v	2.838 (4)	H12···H1	2.3700
N2···O2ⁱⁱ	3.027 (3)	H13···O2ⁱⁱ	2.5400
C2···C18^viii	3.571 (5)	H15···O1	2.5000
C2···O2ⁱⁱⁱ	3.300 (4)	H15···C7ⁱ	2.9300
C4···C5^ix	3.560 (5)	H16···C1ⁱ	3.0600
C5···C5^ix	3.505 (4)	H16···C10	2.7300
C5···C4^ix	3.560 (5)	H16···H10	2.2900
C6···C16^vii	3.579 (4)	H17A···H9	2.1200
C6···O5	3.281 (3)	H17B···O3	2.6300
C7···O6	3.374 (3)	H21···H62^v	2.37 (5)
C7···C15^vii	3.522 (4)	H21···O6^v	1.94 (3)
C13···O3ⁱⁱⁱ	3.364 (4)	H22···O2ⁱⁱ	2.22 (3)
C13···O2ⁱⁱ	3.418 (3)	H61···O5	2.10 (4)
C15···C7ⁱ	3.522 (4)	H61···C7	2.98 (4)
C16···C6ⁱ	3.579 (4)	H61···C8	2.93 (4)
C18···C2^viii	3.571 (5)	H61···C9	2.99 (4)
C1···H16^vii	3.0600	H62···C7	3.06 (3)
C4···H5^ix	2.9100	H62···O4^iv	1.90 (3)
C5···H5^ix	3.0500	H62···H1^iv	2.5000
C7···H15^vii	2.9300	H62···H21^v	2.37 (5)

O1—S1—O2	118.76 (12)	C12—C13—C14	120.0 (2)
O1—S1—N2	107.72 (14)	S1—C14—C13	120.33 (17)
O1—S1—C14	107.54 (11)	S1—C14—C15	120.1 (2)
O2—S1—N2	105.54 (15)	C13—C14—C15	119.5 (2)
O2—S1—C14	107.37 (12)	C14—C15—C16	120.3 (2)
N2—S1—C14	109.74 (15)	C11—C16—C15	119.8 (2)
C1—O3—C9	115.5 (2)	O5—C17—C18	109.0 (3)
C9—O5—C17	112.4 (2)	C1—C2—H2	121.00
H61—O6—H62	112 (3)	C3—C2—H2	121.00
C10—N1—C11	127.0 (2)	C4—C3—H3	119.00
C10—N1—H1	116.00	C2—C3—H3	119.00
C11—N1—H1	117.00	C5—C4—H4	120.00
S1—N2—H22	113 (2)	C3—C4—H4	120.00
H21—N2—H22	119 (3)	C4—C5—H5	120.00
S1—N2—H21	112 (2)	C6—C5—H5	120.00
O3—C1—C2	117.0 (3)	O3—C9—H9	105.4 (14)
O3—C1—C6	122.0 (2)	O5—C9—H9	104.0 (14)
C2—C1—C6	121.0 (3)	C8—C9—H9	116.5 (13)
C1—C2—C3	118.8 (3)	C8—C10—H10	118.00
C2—C3—C4	121.4 (3)	N1—C10—H10	118.00
C3—C4—C5	119.4 (3)	C11—C12—H12	120.00
C4—C5—C6	120.7 (3)	C13—C12—H12	120.00
C1—C6—C7	119.4 (3)	C12—C13—H13	120.00
C1—C6—C5	118.7 (2)	C14—C13—H13	120.00
C5—C6—C7	121.8 (2)	C16—C15—H15	120.00
O4—C7—C6	120.9 (2)	C14—C15—H15	120.00
O4—C7—C8	123.5 (2)	C15—C16—H16	120.00
C6—C7—C8	115.5 (2)	C11—C16—H16	120.00
C7—C8—C10	122.8 (2)	O5—C17—H17A	110.00
C7—C8—C9	118.8 (2)	C18—C17—H17A	110.00
C9—C8—C10	118.3 (3)	C18—C17—H17B	110.00
O3—C9—O5	109.9 (2)	O5—C17—H17B	110.00
O5—C9—C8	108.6 (2)	H17A—C17—H17B	108.00
O3—C9—C8	112.1 (2)	C17—C18—H18B	109.00
N1—C10—C8	124.6 (3)	C17—C18—H18C	110.00
C12—C11—C16	120.1 (2)	C17—C18—H18A	109.00
N1—C11—C16	121.8 (3)	H18A—C18—H18C	109.00
N1—C11—C12	118.1 (2)	H18B—C18—H18C	109.00
C11—C12—C13	120.3 (2)	H18A—C18—H18B	109.00

O1—S1—C14—C13	175.5 (2)	C4—C5—C6—C7	174.1 (3)
O1—S1—C14—C15	−4.3 (3)	C1—C6—C7—O4	162.4 (3)
O2—S1—C14—C13	−55.6 (3)	C1—C6—C7—C8	−15.9 (4)
O2—S1—C14—C15	124.6 (2)	C5—C6—C7—O4	−12.7 (4)
N2—S1—C14—C13	58.6 (3)	C5—C6—C7—C8	169.0 (3)
N2—S1—C14—C15	−121.2 (3)	O4—C7—C8—C9	176.8 (3)
C9—O3—C1—C2	−154.9 (3)	O4—C7—C8—C10	0.5 (4)
C9—O3—C1—C6	28.5 (4)	C6—C7—C8—C9	−4.9 (4)
C1—O3—C9—O5	73.9 (3)	C6—C7—C8—C10	178.7 (3)
C1—O3—C9—C8	−47.0 (3)	C7—C8—C9—O3	35.4 (4)
C17—O5—C9—O3	66.6 (3)	C7—C8—C9—O5	−86.2 (3)
C17—O5—C9—C8	−170.5 (2)	C10—C8—C9—O3	−148.0 (3)
C9—O5—C17—C18	167.6 (3)	C10—C8—C9—O5	90.4 (3)
C11—N1—C10—C8	175.7 (3)	C7—C8—C10—N1	−3.0 (5)
C10—N1—C11—C12	156.4 (3)	C9—C8—C10—N1	−179.4 (3)
C10—N1—C11—C16	−26.2 (4)	N1—C11—C12—C13	178.2 (3)
O3—C1—C2—C3	−179.0 (3)	C16—C11—C12—C13	0.8 (5)
C6—C1—C2—C3	−2.3 (5)	N1—C11—C16—C15	−178.3 (3)
O3—C1—C6—C5	179.6 (3)	C12—C11—C16—C15	−1.0 (5)
O3—C1—C6—C7	4.4 (4)	C11—C12—C13—C14	0.3 (5)
C2—C1—C6—C5	3.1 (4)	C12—C13—C14—S1	179.0 (2)
C2—C1—C6—C7	−172.2 (3)	C12—C13—C14—C15	−1.2 (5)
C1—C2—C3—C4	−0.6 (5)	S1—C14—C15—C16	−179.2 (2)
C2—C3—C4—C5	2.6 (5)	C13—C14—C15—C16	1.0 (5)
C3—C4—C5—C6	−1.7 (5)	C14—C15—C16—C11	0.1 (5)
C4—C5—C6—C1	−1.1 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z−1; (iii) −x, −y, −z; (iv) −x, −y+1, −z; (v) −x+1, −y+1, −z; (vi) −x+1, −y, −z; (vii) x−1, y, z; (viii) −x, −y+1, −z+1; (ix) −x−1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.04	2.696 (3)	132
N2—H21···O6^v	0.91 (3)	1.94 (3)	2.838 (4)	169 (3)
N2—H22···O2ⁱⁱ	0.85 (3)	2.22 (3)	3.027 (3)	159 (3)
O6—H61···O5	0.90 (4)	2.10 (4)	2.999 (3)	176.7 (16)
O6—H62···O4^iv	0.92 (3)	1.90 (3)	2.784 (3)	161 (3)
C2—H2···O2ⁱⁱⁱ	0.93	2.42	3.300 (4)	157
C9—H9···O1^vi	1.04 (3)	2.54 (3)	3.472 (3)	149 (2)
C13—H13···O2ⁱⁱ	0.93	2.54	3.418 (3)	158
C15—H15···O1	0.93	2.50	2.884 (3)	105
C16—H16···Cg1ⁱ	0.93	2.95	3.565 (3)	125

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₅S·H₂O
M_r	392.42
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2727 (6), 10.0166 (8), 11.5830 (9)
α, β, γ (°)	102.480 (5), 97.049 (4), 96.731 (4)
V (Å³)	919.77 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.10 × 0.09

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	18417, 4729, 2022
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.125, 1.00
No. of reflections	4729
No. of parameters	260
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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···O4	0.86	2.04	2.696 (3)	132
N2—H21···O6ⁱ	0.91 (3)	1.94 (3)	2.838 (4)	169 (3)
N2—H22···O2ⁱⁱ	0.85 (3)	2.22 (3)	3.027 (3)	159 (3)
O6—H61···O5	0.90 (4)	2.10 (4)	2.999 (3)	176.7 (16)
O6—H62···O4ⁱⁱⁱ	0.92 (3)	1.90 (3)	2.784 (3)	161 (3)
C2—H2···O2^iv	0.93	2.42	3.300 (4)	157
C9—H9···O1^v	1.04 (3)	2.54 (3)	3.472 (3)	149 (2)
C13—H13···O2ⁱⁱ	0.93	2.54	3.418 (3)	158
C15—H15···O1	0.93	2.50	2.884 (3)	105
C16—H16···Cg1^vi	0.93	2.95	3.565 (3)	125

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore and for technical support, respectively.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Al-Zaydi, K. M., Borik, R. M. & Elnagdi, M. H. (2007). J. Heterocycl. Chem. 44, 1187–1189. CrossRef CAS Google Scholar
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Volume 65| Part 8| August 2009| Pages o1818-o1819

doi:10.1107/S1600536809026154

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

4-[(Z)-(2-Eth­­oxy-4-oxochroman-3-yl­­idene)methyl­amino]benzene­sulfonamide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(Z)-(2-Ethoxy-4-oxochroman-3-ylidene)methylamino]benzenesulfonamide monohydrate