supplementary materials
4-{2-[(5-Bromo-2-hydroxybenzylidene)amino]ethyl}benzenesulfonamide
An ethanol solution (20 ml) of 4-(2-aminoethyl) benzene sulfonamide (0.4005 g, 2 mmol) was added to an ethanol solution (10 ml) of 5-bromosalicylaldehyde
(0.402 g, 2 mmol). The reaction mixture was refluxed for 3 h. The colour of
the solution gradually changed from colourless to greenish yellow. The
solution was cooled to room temperature, filtered and the volume was reduced
to about one-third on the rotary evaporator. The resulting mixture was allowed
to stand for 10 days, after which bright yellow needles of (I) were obtained.
The coordinates of H atoms of NH2 group were refined. The other H atoms were
positioned geometrically with O—H = 0.82, C—H = 0.93 and 0.97 Å for
aromatic and methylene H atoms and constrained to ride on their parent atoms,
with Uiso(H) = xUeq(C, N, O), where x = 1.2 for all H atoms.
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).
4-{2-[(5-Bromo-2-hydroxybenzylidene)amino]ethyl}benzenesulfonamide
top
Crystal data top
| C15H15BrN2O3S | F(000) = 776 |
| Mr = 383.26 | Dx = 1.640 Mg m−3 |
| Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2n | Cell parameters from 2932 reflections |
| a = 50.544 (6) Å | θ = 2.4–28.3° |
| b = 6.3146 (10) Å | µ = 2.80 mm−1 |
| c = 4.8625 (5) Å | T = 296 K |
| V = 1551.9 (3) Å3 | Needle, yellow |
| Z = 4 | 0.28 × 0.14 × 0.12 mm |
Data collection top
Bruker Kappa APEXII CCD
diffractometer | 2844 independent reflections |
| Radiation source: fine-focus sealed tube | 2523 reflections with I > 2σ(I) |
| graphite | Rint = 0.035 |
| Detector resolution: 7.80 pixels mm-1 | θmax = 25.5°, θmin = 2.4° |
| ω scans | h = −52→60 |
Absorption correction: multi-scan
(SADABS; Bruker, 2005) | k = −7→6 |
| Tmin = 0.633, Tmax = 0.714 | l = −5→5 |
| 8263 measured reflections | |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.100 | w = 1/[σ2(Fo2) + 2.7358P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.12 | (Δ/σ)max = 0.001 |
| 2844 reflections | Δρmax = 0.41 e Å−3 |
| 213 parameters | Δρmin = −0.79 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 1212 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.050 (15) |
Crystal data top
| C15H15BrN2O3S | V = 1551.9 (3) Å3 |
| Mr = 383.26 | Z = 4 |
| Orthorhombic, Pna21 | Mo Kα radiation |
| a = 50.544 (6) Å | µ = 2.80 mm−1 |
| b = 6.3146 (10) Å | T = 296 K |
| c = 4.8625 (5) Å | 0.28 × 0.14 × 0.12 mm |
Data collection top
Bruker Kappa APEXII CCD
diffractometer | 2844 independent reflections |
Absorption correction: multi-scan
(SADABS; Bruker, 2005) | 2523 reflections with I > 2σ(I) |
| Tmin = 0.633, Tmax = 0.714 | Rint = 0.035 |
| 8263 measured reflections | θmax = 25.5° |
Refinement top
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.100 | Δρmax = 0.41 e Å−3 |
| S = 1.12 | Δρmin = −0.79 e Å−3 |
| 2844 reflections | Absolute structure: Flack (1983), 1212 Friedel pairs |
| 213 parameters | Flack parameter: 0.050 (15) |
| 1 restraint | |
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 | Uiso*/Ueq | |
| Br1 | 0.24179 (1) | 0.37198 (12) | 1.16449 (17) | 0.0633 (2) | |
| S1 | 0.03204 (2) | −0.2434 (2) | −0.5033 (3) | 0.0276 (3) | |
| O1 | 0.15029 (7) | 0.8114 (6) | 0.6129 (10) | 0.0543 (16) | |
| O2 | 0.04542 (7) | −0.4313 (6) | −0.5921 (8) | 0.0460 (12) | |
| O3 | 0.02060 (7) | −0.1032 (6) | −0.7008 (7) | 0.0398 (11) | |
| N1 | 0.14244 (8) | 0.4653 (8) | 0.3341 (10) | 0.0420 (16) | |
| N2 | 0.00760 (8) | −0.3200 (7) | −0.3108 (12) | 0.0367 (14) | |
| C1 | 0.17777 (8) | 0.5013 (8) | 0.6554 (13) | 0.0330 (14) | |
| C2 | 0.17084 (9) | 0.7071 (9) | 0.7344 (10) | 0.0360 (17) | |
| C3 | 0.18524 (10) | 0.8111 (9) | 0.9375 (12) | 0.0437 (19) | |
| C4 | 0.20599 (10) | 0.7116 (9) | 1.0649 (10) | 0.0403 (19) | |
| C5 | 0.21316 (9) | 0.5108 (9) | 0.9871 (12) | 0.0373 (16) | |
| C6 | 0.19906 (10) | 0.4058 (9) | 0.7859 (11) | 0.0397 (17) | |
| C7 | 0.16276 (10) | 0.3869 (9) | 0.4471 (11) | 0.0390 (17) | |
| C8 | 0.12783 (10) | 0.3344 (9) | 0.1349 (13) | 0.0463 (19) | |
| C9 | 0.10328 (11) | 0.2403 (10) | 0.2692 (11) | 0.0450 (19) | |
| C10 | 0.08639 (10) | 0.1205 (9) | 0.0700 (9) | 0.0330 (16) | |
| C11 | 0.09253 (10) | −0.0829 (9) | −0.0103 (12) | 0.0420 (19) | |
| C12 | 0.07651 (10) | −0.1935 (8) | −0.1920 (12) | 0.0380 (17) | |
| C13 | 0.05431 (8) | −0.0959 (7) | −0.2953 (9) | 0.0263 (16) | |
| C14 | 0.04792 (10) | 0.1065 (8) | −0.2252 (10) | 0.0323 (17) | |
| C15 | 0.06412 (10) | 0.2172 (9) | −0.0426 (12) | 0.0403 (17) | |
| H1O | 0.14259 | 0.73100 | 0.50732 | 0.0815* | |
| H2A | −0.0025 (11) | −0.224 (8) | −0.292 (14) | 0.0439* | |
| H2B | 0.0123 (10) | −0.405 (9) | −0.181 (13) | 0.0439* | |
| H3 | 0.18077 | 0.94875 | 0.98695 | 0.0522* | |
| H4 | 0.21522 | 0.78030 | 1.20423 | 0.0481* | |
| H6 | 0.20392 | 0.26884 | 0.73703 | 0.042 (16)* | |
| H7 | 0.16828 | 0.25207 | 0.39564 | 0.06 (2)* | |
| H8A | 0.13916 | 0.22125 | 0.06878 | 0.0554* | |
| H8B | 0.12268 | 0.42041 | −0.02147 | 0.0554* | |
| H9A | 0.10868 | 0.14594 | 0.41624 | 0.0540* | |
| H9B | 0.09291 | 0.35359 | 0.35006 | 0.0540* | |
| H11 | 0.10770 | −0.14723 | 0.05852 | 0.06 (2)* | |
| H12 | 0.08071 | −0.33135 | −0.24312 | 0.030 (14)* | |
| H14 | 0.03291 | 0.17034 | −0.29820 | 0.040 (14)* | |
| H15 | 0.06003 | 0.35623 | 0.00408 | 0.030 (13)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Br1 | 0.0515 (3) | 0.0879 (5) | 0.0505 (3) | 0.0203 (3) | −0.0093 (4) | −0.0043 (4) |
| S1 | 0.0311 (6) | 0.0282 (6) | 0.0234 (5) | −0.0029 (5) | 0.0027 (5) | −0.0059 (5) |
| O1 | 0.045 (2) | 0.047 (3) | 0.071 (3) | 0.0065 (19) | −0.013 (2) | −0.008 (2) |
| O2 | 0.047 (2) | 0.036 (2) | 0.055 (2) | 0.0026 (18) | 0.0051 (19) | −0.0254 (19) |
| O3 | 0.047 (2) | 0.042 (2) | 0.0305 (18) | −0.0067 (19) | −0.0041 (16) | 0.0036 (17) |
| N1 | 0.030 (2) | 0.052 (3) | 0.044 (3) | −0.010 (2) | −0.001 (2) | −0.009 (2) |
| N2 | 0.040 (2) | 0.036 (3) | 0.034 (2) | −0.0072 (19) | 0.005 (3) | 0.002 (2) |
| C1 | 0.028 (2) | 0.034 (3) | 0.037 (2) | −0.007 (2) | 0.010 (3) | −0.009 (3) |
| C2 | 0.028 (3) | 0.037 (3) | 0.043 (3) | −0.004 (2) | 0.008 (2) | −0.005 (2) |
| C3 | 0.042 (3) | 0.036 (3) | 0.053 (4) | −0.002 (2) | −0.002 (3) | −0.008 (3) |
| C4 | 0.040 (3) | 0.046 (4) | 0.035 (3) | −0.011 (3) | 0.004 (2) | −0.009 (2) |
| C5 | 0.025 (2) | 0.052 (3) | 0.035 (3) | 0.003 (2) | 0.008 (2) | 0.003 (3) |
| C6 | 0.038 (3) | 0.037 (3) | 0.044 (3) | −0.003 (3) | 0.008 (2) | −0.008 (3) |
| C7 | 0.036 (3) | 0.040 (3) | 0.041 (3) | −0.006 (2) | 0.007 (2) | −0.008 (3) |
| C8 | 0.042 (3) | 0.057 (4) | 0.040 (3) | −0.013 (3) | −0.011 (3) | −0.011 (3) |
| C9 | 0.046 (3) | 0.051 (4) | 0.038 (3) | −0.013 (3) | −0.005 (2) | −0.007 (3) |
| C10 | 0.031 (2) | 0.041 (3) | 0.027 (3) | −0.015 (2) | 0.0053 (19) | −0.004 (2) |
| C11 | 0.034 (3) | 0.047 (4) | 0.045 (3) | 0.003 (2) | −0.010 (3) | −0.004 (3) |
| C12 | 0.042 (3) | 0.025 (3) | 0.047 (3) | 0.004 (2) | −0.007 (3) | −0.009 (3) |
| C13 | 0.031 (2) | 0.028 (3) | 0.020 (3) | −0.0034 (19) | 0.004 (2) | −0.003 (2) |
| C14 | 0.030 (3) | 0.028 (3) | 0.039 (3) | −0.002 (2) | −0.002 (2) | −0.002 (2) |
| C15 | 0.045 (3) | 0.034 (3) | 0.042 (3) | −0.004 (2) | 0.005 (3) | −0.011 (3) |
Geometric parameters (Å, °) top
| Br1—C5 | 1.899 (5) | C9—C10 | 1.496 (8) |
| S1—O2 | 1.432 (4) | C10—C15 | 1.393 (7) |
| S1—O3 | 1.428 (4) | C10—C11 | 1.378 (8) |
| S1—N2 | 1.624 (5) | C11—C12 | 1.387 (8) |
| S1—C13 | 1.777 (4) | C12—C13 | 1.375 (7) |
| O1—C2 | 1.364 (6) | C13—C14 | 1.362 (7) |
| O1—H1O | 0.8200 | C14—C15 | 1.396 (7) |
| N1—C7 | 1.266 (7) | C3—H3 | 0.9300 |
| N1—C8 | 1.472 (8) | C4—H4 | 0.9300 |
| N2—H2A | 0.80 (5) | C6—H6 | 0.9300 |
| N2—H2B | 0.86 (6) | C7—H7 | 0.9300 |
| C1—C7 | 1.457 (8) | C8—H8A | 0.9700 |
| C1—C2 | 1.400 (8) | C8—H8B | 0.9700 |
| C1—C6 | 1.387 (7) | C9—H9A | 0.9700 |
| C2—C3 | 1.392 (7) | C9—H9B | 0.9700 |
| C3—C4 | 1.371 (7) | C11—H11 | 0.9300 |
| C4—C5 | 1.372 (8) | C12—H12 | 0.9300 |
| C5—C6 | 1.380 (8) | C14—H14 | 0.9300 |
| C8—C9 | 1.523 (8) | C15—H15 | 0.9300 |
| | | |
| Br1···C6i | 3.720 (5) | C7···C5vi | 3.479 (7) |
| Br1···C4ii | 3.433 (5) | C8···C1vi | 3.594 (8) |
| Br1···C5ii | 3.584 (5) | C13···O3i | 3.356 (6) |
| Br1···H4iii | 3.1700 | C14···O3i | 3.188 (6) |
| O1···N1 | 2.602 (6) | C15···O2x | 3.259 (7) |
| O2···C15iv | 3.259 (7) | C15···O3i | 3.420 (7) |
| O3···N2v | 3.076 (6) | C7···H1O | 2.4200 |
| O3···C14vi | 3.188 (6) | C11···H8A | 3.0600 |
| O3···C15vi | 3.420 (7) | H1O···N1 | 1.8800 |
| O3···C13vi | 3.356 (6) | H1O···C7 | 2.4200 |
| O2···H12 | 2.5400 | H2A···O3vii | 2.30 (5) |
| O2···H15iv | 2.4900 | H2B···N2xi | 2.70 (6) |
| O2···H9Biv | 2.7700 | H4···Br1xii | 3.1700 |
| O3···H14 | 2.6800 | H6···H7 | 2.4500 |
| O3···H2Av | 2.30 (5) | H7···H6 | 2.4500 |
| O3···H14v | 2.7800 | H7···H8A | 2.1700 |
| N1···O1 | 2.602 (6) | H8A···C11 | 3.0600 |
| N2···O3vii | 3.076 (6) | H8A···H7 | 2.1700 |
| N1···H1O | 1.8800 | H9A···H11 | 2.5400 |
| N2···H2Bviii | 2.70 (6) | H9B···O2x | 2.7700 |
| C1···C4vi | 3.470 (8) | H9B···H15 | 2.3600 |
| C1···C8i | 3.594 (8) | H11···H9A | 2.5400 |
| C4···C1i | 3.470 (8) | H12···O2 | 2.5400 |
| C4···C7i | 3.526 (8) | H12···H15xiii | 2.5400 |
| C4···Br1ix | 3.433 (5) | H14···O3 | 2.6800 |
| C5···C7i | 3.479 (7) | H14···O3vii | 2.7800 |
| C5···Br1ix | 3.584 (5) | H15···O2x | 2.4900 |
| C6···Br1vi | 3.720 (5) | H15···H9B | 2.3600 |
| C7···C4vi | 3.526 (8) | H15···H12xiv | 2.5400 |
| | | |
| O2—S1—O3 | 120.1 (2) | S1—C13—C12 | 119.3 (4) |
| O2—S1—N2 | 106.6 (2) | C12—C13—C14 | 121.5 (4) |
| O2—S1—C13 | 107.9 (2) | S1—C13—C14 | 119.0 (3) |
| O3—S1—N2 | 105.3 (2) | C13—C14—C15 | 119.4 (5) |
| O3—S1—C13 | 108.3 (2) | C10—C15—C14 | 120.3 (5) |
| N2—S1—C13 | 108.1 (2) | C2—C3—H3 | 120.00 |
| C2—O1—H1O | 109.00 | C4—C3—H3 | 120.00 |
| C7—N1—C8 | 118.2 (5) | C3—C4—H4 | 120.00 |
| S1—N2—H2A | 109 (4) | C5—C4—H4 | 120.00 |
| S1—N2—H2B | 114 (3) | C1—C6—H6 | 119.00 |
| H2A—N2—H2B | 124 (6) | C5—C6—H6 | 119.00 |
| C2—C1—C7 | 121.4 (4) | N1—C7—H7 | 119.00 |
| C6—C1—C7 | 120.4 (5) | C1—C7—H7 | 119.00 |
| C2—C1—C6 | 118.2 (5) | N1—C8—H8A | 110.00 |
| O1—C2—C1 | 121.3 (5) | N1—C8—H8B | 110.00 |
| O1—C2—C3 | 118.5 (5) | C9—C8—H8A | 110.00 |
| C1—C2—C3 | 120.1 (5) | C9—C8—H8B | 110.00 |
| C2—C3—C4 | 120.3 (5) | H8A—C8—H8B | 108.00 |
| C3—C4—C5 | 120.1 (5) | C8—C9—H9A | 109.00 |
| Br1—C5—C4 | 120.2 (4) | C8—C9—H9B | 109.00 |
| Br1—C5—C6 | 119.6 (4) | C10—C9—H9A | 109.00 |
| C4—C5—C6 | 120.2 (5) | C10—C9—H9B | 109.00 |
| C1—C6—C5 | 121.1 (5) | H9A—C9—H9B | 108.00 |
| N1—C7—C1 | 122.0 (5) | C10—C11—H11 | 119.00 |
| N1—C8—C9 | 110.2 (5) | C12—C11—H11 | 119.00 |
| C8—C9—C10 | 112.6 (4) | C11—C12—H12 | 121.00 |
| C9—C10—C15 | 119.6 (5) | C13—C12—H12 | 121.00 |
| C11—C10—C15 | 118.6 (5) | C13—C14—H14 | 120.00 |
| C9—C10—C11 | 121.8 (5) | C15—C14—H14 | 120.00 |
| C10—C11—C12 | 121.2 (5) | C10—C15—H15 | 120.00 |
| C11—C12—C13 | 118.9 (5) | C14—C15—H15 | 120.00 |
| | | |
| O2—S1—C13—C12 | −16.3 (5) | C2—C3—C4—C5 | 1.9 (8) |
| O2—S1—C13—C14 | 168.7 (4) | C3—C4—C5—Br1 | −179.7 (4) |
| O3—S1—C13—C12 | −147.7 (4) | C3—C4—C5—C6 | −1.9 (8) |
| O3—S1—C13—C14 | 37.2 (4) | Br1—C5—C6—C1 | 178.9 (4) |
| N2—S1—C13—C12 | 98.7 (4) | C4—C5—C6—C1 | 1.1 (8) |
| N2—S1—C13—C14 | −76.4 (4) | N1—C8—C9—C10 | 175.1 (5) |
| C8—N1—C7—C1 | −177.3 (5) | C8—C9—C10—C11 | 79.5 (7) |
| C7—N1—C8—C9 | 101.1 (6) | C8—C9—C10—C15 | −99.3 (6) |
| C6—C1—C2—O1 | 179.3 (5) | C9—C10—C11—C12 | 179.0 (5) |
| C6—C1—C2—C3 | 0.4 (8) | C15—C10—C11—C12 | −2.2 (8) |
| C7—C1—C2—O1 | −2.2 (8) | C9—C10—C15—C14 | −179.0 (5) |
| C7—C1—C2—C3 | 178.8 (5) | C11—C10—C15—C14 | 2.3 (8) |
| C2—C1—C6—C5 | −0.4 (8) | C10—C11—C12—C13 | 0.8 (8) |
| C7—C1—C6—C5 | −178.8 (5) | C11—C12—C13—S1 | −174.3 (4) |
| C2—C1—C7—N1 | −2.0 (8) | C11—C12—C13—C14 | 0.6 (8) |
| C6—C1—C7—N1 | 176.4 (5) | S1—C13—C14—C15 | 174.4 (4) |
| O1—C2—C3—C4 | 179.9 (5) | C12—C13—C14—C15 | −0.5 (7) |
| C1—C2—C3—C4 | −1.2 (8) | C13—C14—C15—C10 | −1.0 (8) |
| Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y−1/2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2; (iv) x, y−1, z−1; (v) −x, −y, z−1/2; (vi) x, y, z−1; (vii) −x, −y, z+1/2; (viii) −x, −y−1, z−1/2; (ix) −x+1/2, y+1/2, z−1/2; (x) x, y+1, z+1; (xi) −x, −y−1, z+1/2; (xii) −x+1/2, y+1/2, z+1/2; (xiii) x, y−1, z; (xiv) x, y+1, z. |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···N1 | 0.82 | 1.88 | 2.602 (6) | 147 |
| N2—H2A···O3vii | 0.80 (5) | 2.30 (5) | 3.076 (6) | 163 (5) |
| C15—H15···O2x | 0.93 | 2.49 | 3.259 (7) | 140 |
| Symmetry codes: (vii) −x, −y, z+1/2; (x) x, y+1, z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···N1 | 0.82 | 1.88 | 2.602 (6) | 147 |
| N2—H2A···O3i | 0.80 (5) | 2.30 (5) | 3.076 (6) | 163 (5) |
| C15—H15···O2ii | 0.93 | 2.49 | 3.259 (7) | 140 |
| Symmetry codes: (i) −x, −y, z+1/2; (ii) x, y+1, z+1. |
HAS greatfully acknowledges the Higher Education Commission, Islamabad,
Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN
042-160410-PS2-117).
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N hydrogen bond helps to establish the conformation. In the crystal structure, the molecules are linked by way of N-H![[Figure 1]](./hb5091fig1thm.gif)
![[Figure 2]](./hb5091fig2thm.gif)
As part of our ongoing studies of sulfonamide derivatives (Chohan et al. 2009), we now report the preparation and crystal structure of title compound (I), (Fig. 1).
The crystal structure of (II) 4-{2-[(5-chloro-2 hydroxybenzylidene)amino]ethyl} -benzenesulfonamide (Chohan et al., 2008) has been reported which differs from (I) due to chloro substitution instead of bromo.
In (I), the benzene rings A (C1–C6) of 5-bromosalicylaldehyde and B (C10–C15) of sulfanilamide moiety are oriented at a dihedral angle of 6.1 (3)° whereas its value as observed in (II) is 23.95 (18)°. The Br1 and S1 atoms are at a distance of -0.024 (7) and -0.167 (6) Å from the mean square planes of rings A and B, respectively. There exist two intramolecular H-bondings (Table 1, Fig. 1) forming S(5) and S(6) ring motifs (Bernstein et al., 1995). Two intermolecular H-bondings (Table 1, Fig. 2) link the molecules in infinite one dimensional polymeric network extending along the c axis.