4-[(E)-({4-[(4-Amino­phen­yl)sulfon­yl]phen­yl}imino)­meth­yl]phenol ethanol monosolvate

Afzal, S.; Akhter, Z.; Tahir, M.N.

doi:10.1107/S1600536812021563

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1789

doi:10.1107/S1600536812021563

Open

access

4-[(E)-({4-[(4-Aminophenyl)sulfonyl]phenyl}imino)methyl]phenol ethanol monosolvate

Sadaf Afzal,^a Zareen Akhter ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 11 May 2012; accepted 11 May 2012; online 19 May 2012)

In the title compound, C₁₉H₁₆N₂O₃S·C₂H₆O, the 4-hydroxybenzylidene group is oriented at dihedral angles of 73.17 (7) and 77.06 (7)° with respect to the aniline groups. The sulfonyl group make dihedral angles of 44.89 (13) and 59.16 (12)° with the adjacent aniline groups. In the crystal, a two-dimensional polymeric network parallel to (010) is formed by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. There also exist π–π interactions with a distance of 3.5976 (18) Å between the centroids of hydroxyphenyl rings.

Related literature

For related structures, see: Bocelli & Cantoni (1990 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₃S·C₂H₆O
M_r = 398.47
Monoclinic, P 2₁ /n
a = 8.5281 (3) Å
b = 25.3057 (12) Å
c = 9.4084 (4) Å
β = 96.738 (3)°
V = 2016.40 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.948, T_max = 0.968
16497 measured reflections
3969 independent reflections
2400 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.138
S = 1.04
3969 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.22 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
O1—H1⋯O4ⁱ	0.82	1.89	2.698 (3)	171
N2—H2A⋯O3ⁱⁱ	0.86	2.30	3.105 (3)	156
N2—H2B⋯O2ⁱⁱⁱ	0.86	2.21	3.026 (3)	157
O4—H4⋯N1^iv	0.82	2.13	2.926 (3)	162
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x-1, y, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z+1.

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/S1600536812021563/bq2358sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021563/bq2358Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021563/bq2358Isup3.cml

checkCIF report

Comment top

The structure of 4,4'-diamino-diphenylsulfone (Bocelli & Cantoni, 1990), related to the title compound, (I), shown in Fig. 1., has been published previously. In (I), the 4-hydroxybenzaldehyde moiety A (O1/C1–C7), the anilinic moieties of 4,4'-diaminodiphenylsulfone B (N1/C8—C13) and C (C14—C19/N2) are planar with r.m.s. deviation of 0.0125 Å, 0.0320 Å and 0.0151 Å, respectively. The dihedral angles between A/B, A/C and B/C are 73.17 (7)°, 77.06 (7)° and 77.16 (7)°, respectively. The sulfonyl group D (O2/S1/O3) is of course planar. The dihedral angles between B/D and C/D are 59.16 (12)° and 44.89 (13)°, respectively. The molecules are stabilized in the form of two-dimensional polymeric network due to various type of H-bondings (Table 1, Fig. 2). There exist also π–π interaction between the CgA···CgAⁱ [i = 1 - x,-y, 2 - z] at a distance of 3.5976 (18) Å, where CgA is the centroid of phenyl ring (C1—C6).

Related literature top

For related structures, see: Bocelli & Cantoni (1990)

Experimental top

In a 250 ml two-necked round bottomed flask equipped with condenser and magnetic stirrer, 4-hydroxy benzaldehyde (1.22 g, 0.01 mole) was dissolved in 50 ml of dried ethanol under inert atmosphere of nitrogen gas. 4,4'-diaminodiphenylsulfone (1.24 g, 0.005 mole) was added to it. The reaction mixture was refluxed for 6 h with constant stirring, and the progress of the reaction was monitored by TLC [n-hexane/ethanol (3:1)] respectively. The yellow colored product thus obtained was filtered, dried and hence recrystallized in ethanol. Yield: 88%, m.p.: 385 K.

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 displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form two dimensional polymeric network. The H-atoms not involved in H-bondings are omitted for clarity.

4-[(E)-({4-[(4-Aminophenyl)sulfonyl]phenyl}imino)methyl]phenol ethanol monosolvate top

Crystal data top

C₁₉H₁₆N₂O₃S·C₂H₆O	F(000) = 840
M_r = 398.47	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2522 reflections
a = 8.5281 (3) Å	θ = 1.6–26.0°
b = 25.3057 (12) Å	µ = 0.19 mm⁻¹
c = 9.4084 (4) Å	T = 296 K
β = 96.738 (3)°	Prism, yellow
V = 2016.40 (15) Å³	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3969 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −28→31
T_min = 0.948, T_max = 0.968	l = −11→11
16497 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0486P)² + 0.7969P] where P = (F_o² + 2F_c²)/3
3969 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₃S·C₂H₆O	V = 2016.40 (15) Å³
M_r = 398.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5281 (3) Å	µ = 0.19 mm⁻¹
b = 25.3057 (12) Å	T = 296 K
c = 9.4084 (4) Å	0.35 × 0.25 × 0.20 mm
β = 96.738 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3969 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2400 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.968	R_int = 0.039
16497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
3969 reflections	Δρ_min = −0.22 e Å⁻³
256 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	0.16578 (8)	0.17666 (3)	0.09119 (8)	0.0587 (3)
O1	0.4083 (3)	−0.10515 (8)	1.1540 (2)	0.0809 (9)
O2	0.1370 (3)	0.14540 (8)	−0.0375 (2)	0.0721 (8)
O3	0.2983 (2)	0.21201 (8)	0.1066 (2)	0.0758 (8)
N1	0.2707 (3)	0.01949 (9)	0.5599 (3)	0.0605 (9)
N2	−0.4161 (3)	0.28543 (11)	0.1989 (3)	0.0851 (11)
C1	0.3681 (3)	−0.07205 (11)	1.0424 (3)	0.0588 (11)
C2	0.4236 (4)	−0.08302 (12)	0.9138 (4)	0.0721 (14)
C3	0.3891 (4)	−0.05033 (12)	0.7990 (3)	0.0682 (12)
C4	0.2988 (3)	−0.00543 (11)	0.8088 (3)	0.0562 (10)
C5	0.2454 (4)	0.00539 (13)	0.9378 (3)	0.0764 (14)
C6	0.2771 (4)	−0.02806 (13)	1.0536 (3)	0.0763 (14)
C7	0.2612 (3)	0.03107 (11)	0.6889 (3)	0.0609 (11)
C8	0.2394 (3)	0.05957 (11)	0.4557 (3)	0.0555 (10)
C9	0.1327 (3)	0.04922 (12)	0.3366 (3)	0.0638 (11)
C10	0.1075 (3)	0.08533 (11)	0.2278 (3)	0.0602 (11)
C11	0.1906 (3)	0.13213 (10)	0.2355 (3)	0.0514 (10)
C12	0.2935 (3)	0.14365 (12)	0.3551 (3)	0.0653 (11)
C13	0.3182 (3)	0.10741 (12)	0.4654 (3)	0.0659 (11)
C14	−0.0044 (3)	0.21204 (10)	0.1125 (3)	0.0484 (9)
C15	−0.1499 (3)	0.19453 (11)	0.0475 (3)	0.0565 (10)
C16	−0.2849 (3)	0.21927 (12)	0.0754 (3)	0.0595 (11)
C17	−0.2800 (3)	0.26199 (11)	0.1685 (3)	0.0548 (10)
C18	−0.1330 (3)	0.28033 (11)	0.2303 (3)	0.0556 (10)
C19	0.0020 (3)	0.25527 (11)	0.2027 (3)	0.0561 (10)
O4	0.7066 (3)	0.07876 (9)	0.6003 (2)	0.0849 (10)
C20	0.8298 (5)	0.11197 (18)	0.5671 (5)	0.1181 (19)
C21	0.7841 (6)	0.15143 (18)	0.4597 (5)	0.134 (2)
H1	0.37154	−0.09407	1.22496	0.0971*
H2	0.48515	−0.11294	0.90520	0.0862*
H2A	−0.50591	0.27377	0.16033	0.1019*
H2B	−0.41223	0.31187	0.25664	0.1019*
H3	0.42698	−0.05840	0.71280	0.0817*
H5	0.18667	0.03587	0.94737	0.0913*
H6	0.23672	−0.02068	1.13905	0.0918*
H7	0.22811	0.06497	0.70918	0.0731*
H9	0.07762	0.01743	0.33023	0.0765*
H10	0.03426	0.07826	0.14877	0.0723*
H12	0.34661	0.17582	0.36174	0.0784*
H13	0.38791	0.11523	0.54620	0.0789*
H15	−0.15513	0.16594	−0.01499	0.0678*
H16	−0.38177	0.20736	0.03146	0.0714*
H18	−0.12709	0.30965	0.29026	0.0667*
H19	0.09933	0.26744	0.24512	0.0673*
H4	0.69645	0.05409	0.54350	0.1018*
H20A	0.91206	0.09020	0.53444	0.1417*
H20B	0.87447	0.12966	0.65393	0.1417*
H21A	0.74450	0.13442	0.37156	0.2008*
H21B	0.87416	0.17265	0.44508	0.2008*
H21C	0.70331	0.17353	0.49098	0.2008*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0582 (4)	0.0594 (5)	0.0613 (5)	0.0032 (4)	0.0187 (3)	0.0088 (4)
O1	0.1062 (18)	0.0712 (14)	0.0637 (15)	0.0133 (12)	0.0030 (13)	0.0100 (12)
O2	0.0955 (15)	0.0701 (13)	0.0547 (14)	0.0147 (11)	0.0260 (11)	0.0005 (11)
O3	0.0545 (12)	0.0784 (14)	0.0973 (17)	−0.0049 (10)	0.0206 (11)	0.0223 (12)
N1	0.0746 (16)	0.0550 (15)	0.0515 (17)	0.0026 (12)	0.0056 (12)	0.0024 (13)
N2	0.0591 (16)	0.099 (2)	0.094 (2)	0.0173 (14)	−0.0038 (14)	−0.0306 (17)
C1	0.0683 (18)	0.0521 (18)	0.053 (2)	−0.0043 (14)	−0.0049 (15)	−0.0015 (15)
C2	0.080 (2)	0.061 (2)	0.078 (3)	0.0171 (16)	0.0202 (18)	0.0090 (18)
C3	0.077 (2)	0.064 (2)	0.066 (2)	0.0050 (16)	0.0190 (16)	0.0022 (17)
C4	0.0611 (17)	0.0522 (17)	0.0537 (19)	−0.0027 (14)	−0.0005 (14)	−0.0060 (15)
C5	0.105 (3)	0.067 (2)	0.056 (2)	0.0257 (18)	0.0040 (18)	−0.0072 (17)
C6	0.108 (3)	0.076 (2)	0.045 (2)	0.024 (2)	0.0099 (17)	−0.0013 (17)
C7	0.0653 (18)	0.0539 (18)	0.062 (2)	0.0012 (14)	0.0012 (15)	−0.0033 (16)
C8	0.0614 (17)	0.0513 (17)	0.0546 (19)	0.0060 (14)	0.0105 (14)	0.0014 (15)
C9	0.077 (2)	0.0543 (18)	0.060 (2)	−0.0126 (15)	0.0077 (16)	−0.0033 (16)
C10	0.0671 (18)	0.0615 (19)	0.0513 (19)	−0.0070 (15)	0.0037 (14)	−0.0017 (16)
C11	0.0494 (15)	0.0525 (17)	0.0538 (19)	0.0056 (13)	0.0128 (13)	−0.0009 (14)
C12	0.0622 (18)	0.0519 (18)	0.080 (2)	−0.0065 (14)	0.0004 (16)	0.0059 (17)
C13	0.0654 (18)	0.064 (2)	0.064 (2)	−0.0024 (15)	−0.0103 (15)	0.0039 (17)
C14	0.0526 (16)	0.0446 (16)	0.0484 (17)	−0.0006 (12)	0.0076 (12)	0.0003 (13)
C15	0.0623 (18)	0.0548 (17)	0.0516 (18)	−0.0093 (14)	0.0029 (14)	−0.0106 (14)
C16	0.0509 (17)	0.070 (2)	0.0550 (19)	−0.0057 (14)	−0.0043 (13)	−0.0053 (16)
C17	0.0552 (17)	0.0585 (18)	0.0493 (18)	0.0055 (14)	0.0007 (13)	0.0022 (14)
C18	0.0622 (18)	0.0495 (16)	0.0535 (18)	−0.0006 (14)	0.0003 (14)	−0.0087 (14)
C19	0.0496 (16)	0.0608 (18)	0.0568 (19)	−0.0082 (13)	0.0019 (13)	−0.0012 (15)
O4	0.1173 (19)	0.0697 (15)	0.0691 (16)	−0.0090 (14)	0.0174 (14)	−0.0028 (12)
C20	0.097 (3)	0.113 (3)	0.146 (4)	−0.026 (3)	0.022 (3)	0.017 (3)
C21	0.192 (5)	0.107 (3)	0.098 (3)	−0.055 (3)	−0.001 (3)	0.017 (3)

Geometric parameters (Å, º) top

S1—O2	1.443 (2)	C14—C15	1.390 (4)
S1—O3	1.435 (2)	C14—C19	1.382 (4)
S1—C11	1.758 (3)	C15—C16	1.363 (4)
S1—C14	1.737 (3)	C16—C17	1.389 (4)
O1—C1	1.355 (3)	C17—C18	1.398 (4)
O1—H1	0.8200	C18—C19	1.366 (4)
O4—C20	1.409 (5)	C2—H2	0.9300
O4—H4	0.8200	C3—H3	0.9300
N1—C7	1.260 (4)	C5—H5	0.9300
N1—C8	1.414 (4)	C6—H6	0.9300
N2—C17	1.363 (4)	C7—H7	0.9300
N2—H2B	0.8600	C9—H9	0.9300
N2—H2A	0.8600	C10—H10	0.9300
C1—C6	1.368 (4)	C12—H12	0.9300
C1—C2	1.378 (5)	C13—H13	0.9300
C2—C3	1.365 (5)	C15—H15	0.9300
C3—C4	1.382 (4)	C16—H16	0.9300
C4—C5	1.373 (4)	C18—H18	0.9300
C4—C7	1.464 (4)	C19—H19	0.9300
C5—C6	1.381 (4)	C20—C21	1.441 (7)
C8—C13	1.382 (4)	C20—H20A	0.9700
C8—C9	1.383 (4)	C20—H20B	0.9700
C9—C10	1.370 (4)	C21—H21A	0.9600
C10—C11	1.378 (4)	C21—H21B	0.9600
C11—C12	1.375 (4)	C21—H21C	0.9600
C12—C13	1.382 (4)

O2—S1—O3	118.74 (13)	C17—C18—C19	120.1 (3)
O2—S1—C11	106.85 (12)	C14—C19—C18	120.7 (2)
O2—S1—C14	108.50 (14)	C1—C2—H2	120.00
O3—S1—C11	107.43 (12)	C3—C2—H2	120.00
O3—S1—C14	109.01 (12)	C4—C3—H3	119.00
C11—S1—C14	105.53 (13)	C2—C3—H3	119.00
C1—O1—H1	109.00	C4—C5—H5	119.00
C20—O4—H4	110.00	C6—C5—H5	119.00
C7—N1—C8	118.2 (2)	C5—C6—H6	120.00
C17—N2—H2B	120.00	C1—C6—H6	120.00
H2A—N2—H2B	120.00	N1—C7—H7	118.00
C17—N2—H2A	120.00	C4—C7—H7	118.00
C2—C1—C6	119.2 (3)	C8—C9—H9	120.00
O1—C1—C2	118.3 (3)	C10—C9—H9	120.00
O1—C1—C6	122.5 (3)	C11—C10—H10	120.00
C1—C2—C3	120.6 (3)	C9—C10—H10	120.00
C2—C3—C4	121.0 (3)	C13—C12—H12	120.00
C5—C4—C7	119.3 (3)	C11—C12—H12	120.00
C3—C4—C7	122.7 (3)	C8—C13—H13	120.00
C3—C4—C5	117.9 (3)	C12—C13—H13	120.00
C4—C5—C6	121.4 (3)	C14—C15—H15	120.00
C1—C6—C5	119.9 (3)	C16—C15—H15	120.00
N1—C7—C4	124.2 (3)	C17—C16—H16	119.00
C9—C8—C13	119.2 (3)	C15—C16—H16	119.00
N1—C8—C13	122.1 (2)	C17—C18—H18	120.00
N1—C8—C9	118.6 (3)	C19—C18—H18	120.00
C8—C9—C10	120.6 (3)	C18—C19—H19	120.00
C9—C10—C11	120.0 (3)	C14—C19—H19	120.00
C10—C11—C12	120.0 (3)	O4—C20—C21	114.9 (4)
S1—C11—C10	119.7 (2)	O4—C20—H20A	109.00
S1—C11—C12	120.3 (2)	O4—C20—H20B	109.00
C11—C12—C13	120.0 (3)	C21—C20—H20A	109.00
C8—C13—C12	120.1 (3)	C21—C20—H20B	109.00
S1—C14—C19	120.4 (2)	H20A—C20—H20B	108.00
C15—C14—C19	119.4 (2)	C20—C21—H21A	109.00
S1—C14—C15	120.0 (2)	C20—C21—H21B	109.00
C14—C15—C16	120.0 (3)	C20—C21—H21C	109.00
C15—C16—C17	121.0 (2)	H21A—C21—H21B	109.00
C16—C17—C18	118.7 (2)	H21A—C21—H21C	109.00
N2—C17—C18	120.8 (3)	H21B—C21—H21C	109.00
N2—C17—C16	120.5 (2)

O2—S1—C11—C10	−33.3 (3)	C3—C4—C7—N1	18.7 (4)
O2—S1—C11—C12	146.1 (2)	C5—C4—C7—N1	−162.5 (3)
O3—S1—C11—C10	−161.7 (2)	C4—C5—C6—C1	2.3 (5)
O3—S1—C11—C12	17.7 (3)	N1—C8—C9—C10	−175.1 (3)
C14—S1—C11—C10	82.1 (2)	C13—C8—C9—C10	1.4 (4)
C14—S1—C11—C12	−98.5 (2)	N1—C8—C13—C12	174.5 (3)
O2—S1—C14—C15	22.7 (3)	C9—C8—C13—C12	−1.9 (4)
O2—S1—C14—C19	−162.3 (2)	C8—C9—C10—C11	1.0 (4)
O3—S1—C14—C15	153.4 (2)	C9—C10—C11—S1	176.5 (2)
O3—S1—C14—C19	−31.7 (3)	C9—C10—C11—C12	−2.9 (4)
C11—S1—C14—C15	−91.5 (2)	S1—C11—C12—C13	−176.9 (2)
C11—S1—C14—C19	83.5 (2)	C10—C11—C12—C13	2.5 (4)
C8—N1—C7—C4	−176.5 (2)	C11—C12—C13—C8	−0.1 (4)
C7—N1—C8—C9	−129.1 (3)	S1—C14—C15—C16	173.6 (2)
C7—N1—C8—C13	54.6 (4)	C19—C14—C15—C16	−1.4 (4)
O1—C1—C2—C3	−178.7 (3)	S1—C14—C19—C18	−173.9 (2)
C6—C1—C2—C3	0.3 (5)	C15—C14—C19—C18	1.1 (4)
O1—C1—C6—C5	177.3 (3)	C14—C15—C16—C17	−0.1 (4)
C2—C1—C6—C5	−1.7 (5)	C15—C16—C17—N2	−178.0 (3)
C1—C2—C3—C4	0.4 (5)	C15—C16—C17—C18	1.9 (4)
C2—C3—C4—C5	0.3 (5)	N2—C17—C18—C19	177.7 (3)
C2—C3—C4—C7	179.0 (3)	C16—C17—C18—C19	−2.2 (4)
C3—C4—C5—C6	−1.6 (5)	C17—C18—C19—C14	0.8 (4)
C7—C4—C5—C6	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.89	2.698 (3)	171
N2—H2A···O3ⁱⁱ	0.86	2.30	3.105 (3)	156
N2—H2B···O2ⁱⁱⁱ	0.86	2.21	3.026 (3)	157
O4—H4···N1^iv	0.82	2.13	2.926 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₃S·C₂H₆O
M_r	398.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.5281 (3), 25.3057 (12), 9.4084 (4)
β (°)	96.738 (3)
V (Å³)	2016.40 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.948, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	16497, 3969, 2400
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.138, 1.04
No. of reflections	3969
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

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
O1—H1···O4ⁱ	0.82	1.89	2.698 (3)	171
N2—H2A···O3ⁱⁱ	0.86	2.30	3.105 (3)	156
N2—H2B···O2ⁱⁱⁱ	0.86	2.21	3.026 (3)	157
O4—H4···N1^iv	0.82	2.13	2.926 (3)	162

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

Acknowledgements

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

References

Bocelli, G. & Cantoni, A. (1990). Acta Cryst. C46, 2257–2259. CSD CrossRef CAS Web of Science IUCr Journals 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1789

doi:10.1107/S1600536812021563

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-[(E)-({4-[(4-Amino­phen­yl)sulfon­yl]phen­yl}imino)­meth­yl]phenol ethanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(E)-({4-[(4-Aminophenyl)sulfonyl]phenyl}imino)methyl]phenol ethanol monosolvate