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The crystal structure of the title sulfonamide, C
16H
18N
2O
4S, is stabilized by strong N—H
O and O—H
O intermolecular hydrogen bonds.
Supporting information
CCDC reference: 633863
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.003 Å
- R factor = 0.039
- wR factor = 0.111
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: MSC/AFC7 Diffractometer Control for Windows
(Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-2-(4-hydroxyphenyl)acetamide
top
Crystal data top
C16H18N2O4S | F(000) = 704 |
Mr = 334.39 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 15.715 (3) Å | θ = 12.8–17.2° |
b = 10.250 (2) Å | µ = 0.23 mm−1 |
c = 9.819 (3) Å | T = 295 K |
β = 91.862 (18)° | Prism, colorless |
V = 1580.8 (6) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.037 |
Radiation source: Rigaku rotating anode | θmax = 25.0°, θmin = 2.6° |
Graphite monochromator | h = −18→18 |
ω–2θ scans | k = 0→12 |
3219 measured reflections | l = −11→5 |
2779 independent reflections | 3 standard reflections every 150 reflections |
2100 reflections with I > 2σ(I) | intensity decay: 0.8% |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3548P] where P = (Fo2 + 2Fc2)/3 |
2779 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
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 | |
S1 | 0.15036 (3) | 0.16214 (6) | 0.45805 (5) | 0.0412 (2) | |
O4 | 0.12798 (10) | −0.44728 (16) | 0.39567 (16) | 0.0494 (5) | |
O8 | −0.22426 (9) | −0.18689 (15) | −0.09475 (14) | 0.0451 (5) | |
O11 | 0.13205 (11) | 0.21505 (19) | 0.58883 (14) | 0.0564 (6) | |
O12 | 0.20507 (11) | 0.05214 (17) | 0.4487 (2) | 0.0623 (6) | |
N1 | −0.17633 (10) | −0.17636 (17) | 0.12408 (16) | 0.0355 (5) | |
N2 | 0.19320 (11) | 0.27858 (19) | 0.37363 (17) | 0.0420 (6) | |
C1 | −0.05157 (12) | −0.3702 (2) | 0.08473 (19) | 0.0338 (6) | |
C2 | 0.02723 (14) | −0.3102 (2) | 0.0851 (2) | 0.0423 (7) | |
C3 | 0.08824 (13) | −0.3331 (2) | 0.1876 (2) | 0.0436 (7) | |
C4 | 0.07026 (12) | −0.4176 (2) | 0.2912 (2) | 0.0357 (6) | |
C5 | −0.00737 (13) | −0.4800 (2) | 0.2933 (2) | 0.0426 (7) | |
C6 | −0.06737 (13) | −0.4556 (2) | 0.1892 (2) | 0.0429 (7) | |
C7 | −0.11813 (14) | −0.3411 (2) | −0.0252 (2) | 0.0423 (7) | |
C8 | −0.17668 (12) | −0.2283 (2) | 0.00006 (19) | 0.0335 (6) | |
C9 | −0.22572 (13) | −0.0639 (2) | 0.1634 (2) | 0.0405 (7) | |
C10 | −0.18061 (15) | 0.0649 (2) | 0.1401 (2) | 0.0509 (8) | |
C11 | −0.09913 (14) | 0.0831 (2) | 0.2251 (2) | 0.0401 (7) | |
C12 | −0.09757 (14) | 0.1574 (2) | 0.3431 (2) | 0.0465 (8) | |
C13 | −0.02252 (14) | 0.1782 (2) | 0.4179 (2) | 0.0447 (7) | |
C14 | 0.05229 (13) | 0.1235 (2) | 0.3745 (2) | 0.0360 (6) | |
C15 | 0.05157 (14) | 0.0448 (2) | 0.2602 (2) | 0.0439 (7) | |
C16 | −0.02385 (15) | 0.0254 (2) | 0.1868 (2) | 0.0459 (7) | |
H1 | −0.14430 | −0.21220 | 0.18570 | 0.0400* | |
H2 | 0.03950 | −0.25120 | 0.01350 | 0.0480* | |
H2A | 0.19840 | 0.25350 | 0.29010 | 0.0500* | |
H2B | 0.15930 | 0.34540 | 0.37370 | 0.0500* | |
H3 | 0.14210 | −0.29150 | 0.18490 | 0.0500* | |
H4 | 0.17480 | −0.40590 | 0.38360 | 0.0540* | |
H5 | −0.02000 | −0.53810 | 0.36570 | 0.0480* | |
H6 | −0.12050 | −0.49960 | 0.18980 | 0.0480* | |
H7A | −0.08930 | −0.32440 | −0.10770 | 0.0480* | |
H7B | −0.15230 | −0.41760 | −0.03770 | 0.0480* | |
H9A | −0.27800 | −0.06330 | 0.11150 | 0.0460* | |
H9B | −0.23760 | −0.07100 | 0.25760 | 0.0460* | |
H10A | −0.16730 | 0.07070 | 0.04720 | 0.0570* | |
H10B | −0.21830 | 0.13400 | 0.16270 | 0.0570* | |
H12 | −0.14930 | 0.19450 | 0.37360 | 0.0530* | |
H13 | −0.02250 | 0.22950 | 0.49890 | 0.0510* | |
H15 | 0.10260 | 0.00390 | 0.23240 | 0.0500* | |
H16 | −0.02470 | −0.02860 | 0.10740 | 0.0520* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0421 (3) | 0.0505 (4) | 0.0304 (3) | 0.0041 (3) | −0.0091 (2) | 0.0032 (2) |
O4 | 0.0431 (9) | 0.0567 (10) | 0.0473 (9) | −0.0056 (8) | −0.0174 (7) | 0.0110 (8) |
O8 | 0.0431 (8) | 0.0640 (10) | 0.0274 (7) | 0.0104 (8) | −0.0111 (6) | −0.0017 (7) |
O11 | 0.0604 (10) | 0.0844 (13) | 0.0237 (7) | −0.0005 (9) | −0.0088 (7) | −0.0011 (8) |
O12 | 0.0535 (10) | 0.0580 (11) | 0.0745 (12) | 0.0169 (9) | −0.0133 (9) | 0.0058 (10) |
N1 | 0.0327 (9) | 0.0468 (10) | 0.0262 (8) | 0.0058 (8) | −0.0096 (7) | −0.0033 (7) |
N2 | 0.0409 (10) | 0.0525 (11) | 0.0322 (9) | 0.0001 (9) | −0.0067 (8) | −0.0013 (8) |
C1 | 0.0300 (10) | 0.0405 (11) | 0.0307 (10) | 0.0033 (9) | −0.0028 (8) | −0.0045 (9) |
C2 | 0.0395 (12) | 0.0469 (13) | 0.0403 (12) | −0.0022 (10) | −0.0004 (9) | 0.0118 (10) |
C3 | 0.0312 (11) | 0.0465 (13) | 0.0525 (13) | −0.0055 (10) | −0.0055 (9) | 0.0084 (11) |
C4 | 0.0345 (10) | 0.0387 (12) | 0.0335 (11) | 0.0017 (9) | −0.0069 (8) | −0.0005 (9) |
C5 | 0.0411 (12) | 0.0505 (14) | 0.0361 (12) | −0.0063 (10) | −0.0014 (9) | 0.0117 (10) |
C6 | 0.0316 (11) | 0.0517 (14) | 0.0452 (13) | −0.0082 (10) | −0.0005 (9) | 0.0002 (11) |
C7 | 0.0421 (12) | 0.0529 (13) | 0.0312 (11) | 0.0046 (10) | −0.0076 (9) | −0.0052 (10) |
C8 | 0.0280 (9) | 0.0455 (12) | 0.0267 (10) | −0.0023 (9) | −0.0051 (8) | −0.0004 (9) |
C9 | 0.0331 (11) | 0.0563 (14) | 0.0315 (11) | 0.0073 (10) | −0.0102 (8) | −0.0078 (10) |
C10 | 0.0548 (14) | 0.0478 (14) | 0.0489 (14) | 0.0088 (11) | −0.0182 (11) | 0.0004 (11) |
C11 | 0.0460 (12) | 0.0339 (11) | 0.0397 (11) | −0.0008 (10) | −0.0088 (9) | 0.0031 (9) |
C12 | 0.0406 (12) | 0.0444 (13) | 0.0540 (14) | 0.0097 (10) | −0.0049 (10) | −0.0096 (11) |
C13 | 0.0461 (13) | 0.0478 (13) | 0.0399 (12) | 0.0058 (11) | −0.0024 (10) | −0.0136 (10) |
C14 | 0.0390 (11) | 0.0371 (11) | 0.0315 (10) | −0.0002 (9) | −0.0036 (8) | 0.0007 (9) |
C15 | 0.0419 (12) | 0.0486 (13) | 0.0415 (12) | −0.0001 (10) | 0.0042 (10) | −0.0079 (10) |
C16 | 0.0530 (14) | 0.0502 (13) | 0.0345 (11) | −0.0068 (11) | 0.0017 (10) | −0.0105 (10) |
Geometric parameters (Å, º) top
S1—O11 | 1.4318 (16) | C10—C11 | 1.517 (3) |
S1—O12 | 1.4227 (19) | C11—C12 | 1.386 (3) |
S1—N2 | 1.613 (2) | C11—C16 | 1.386 (3) |
S1—C14 | 1.767 (2) | C12—C13 | 1.386 (3) |
O4—C4 | 1.381 (3) | C13—C14 | 1.382 (3) |
O8—C8 | 1.249 (2) | C14—C15 | 1.382 (3) |
O4—H4 | 0.8600 | C15—C16 | 1.381 (3) |
N1—C9 | 1.449 (3) | C2—H2 | 0.9500 |
N1—C8 | 1.329 (3) | C3—H3 | 0.9500 |
N1—H1 | 0.8600 | C5—H5 | 0.9500 |
N2—H2A | 0.8700 | C6—H6 | 0.9500 |
N2—H2B | 0.8700 | C7—H7A | 0.9600 |
C1—C2 | 1.383 (3) | C7—H7B | 0.9600 |
C1—C6 | 1.377 (3) | C9—H9A | 0.9500 |
C1—C7 | 1.508 (3) | C9—H9B | 0.9500 |
C2—C3 | 1.387 (3) | C10—H10A | 0.9400 |
C3—C4 | 1.372 (3) | C10—H10B | 0.9500 |
C4—C5 | 1.378 (3) | C12—H12 | 0.9500 |
C5—C6 | 1.391 (3) | C13—H13 | 0.9500 |
C7—C8 | 1.503 (3) | C15—H15 | 0.9500 |
C9—C10 | 1.519 (3) | C16—H16 | 0.9600 |
| | | |
O11—S1—O12 | 119.84 (11) | S1—C14—C15 | 119.46 (16) |
O11—S1—N2 | 106.27 (11) | C13—C14—C15 | 120.17 (19) |
O11—S1—C14 | 107.67 (10) | C14—C15—C16 | 119.5 (2) |
O12—S1—N2 | 106.86 (10) | C11—C16—C15 | 121.51 (19) |
O12—S1—C14 | 108.19 (11) | C1—C2—H2 | 119.00 |
N2—S1—C14 | 107.43 (9) | C3—C2—H2 | 119.00 |
C4—O4—H4 | 109.00 | C2—C3—H3 | 120.00 |
C8—N1—C9 | 125.21 (17) | C4—C3—H3 | 121.00 |
C9—N1—H1 | 117.00 | C4—C5—H5 | 120.00 |
C8—N1—H1 | 117.00 | C6—C5—H5 | 121.00 |
H2A—N2—H2B | 108.00 | C1—C6—H6 | 119.00 |
S1—N2—H2B | 108.00 | C5—C6—H6 | 119.00 |
S1—N2—H2A | 109.00 | C1—C7—H7A | 108.00 |
C6—C1—C7 | 121.41 (18) | C1—C7—H7B | 108.00 |
C2—C1—C6 | 117.64 (18) | C8—C7—H7A | 108.00 |
C2—C1—C7 | 120.94 (18) | C8—C7—H7B | 108.00 |
C1—C2—C3 | 121.63 (19) | H7A—C7—H7B | 109.00 |
C2—C3—C4 | 119.37 (19) | N1—C9—H9A | 109.00 |
O4—C4—C5 | 116.55 (18) | N1—C9—H9B | 109.00 |
O4—C4—C3 | 122.92 (18) | C10—C9—H9A | 108.00 |
C3—C4—C5 | 120.51 (18) | C10—C9—H9B | 109.00 |
C4—C5—C6 | 119.01 (19) | H9A—C9—H9B | 109.00 |
C1—C6—C5 | 121.83 (19) | C9—C10—H10A | 109.00 |
C1—C7—C8 | 116.62 (17) | C9—C10—H10B | 108.00 |
O8—C8—C7 | 119.55 (17) | C11—C10—H10A | 108.00 |
N1—C8—C7 | 118.36 (17) | C11—C10—H10B | 107.00 |
O8—C8—N1 | 122.09 (18) | H10A—C10—H10B | 110.00 |
N1—C9—C10 | 113.24 (17) | C11—C12—H12 | 119.00 |
C9—C10—C11 | 114.43 (17) | C13—C12—H12 | 119.00 |
C12—C11—C16 | 118.0 (2) | C12—C13—H13 | 120.00 |
C10—C11—C16 | 120.73 (18) | C14—C13—H13 | 120.00 |
C10—C11—C12 | 121.27 (19) | C14—C15—H15 | 120.00 |
C11—C12—C13 | 121.3 (2) | C16—C15—H15 | 120.00 |
C12—C13—C14 | 119.48 (19) | C11—C16—H16 | 119.00 |
S1—C14—C13 | 120.24 (16) | C15—C16—H16 | 120.00 |
| | | |
O11—S1—C14—C13 | 18.5 (2) | C3—C4—C5—C6 | −0.3 (3) |
O11—S1—C14—C15 | −165.63 (17) | O4—C4—C5—C6 | −178.84 (18) |
O12—S1—C14—C13 | 149.33 (17) | C4—C5—C6—C1 | −0.5 (3) |
O12—S1—C14—C15 | −34.8 (2) | C1—C7—C8—O8 | 169.19 (18) |
N2—S1—C14—C13 | −95.63 (18) | C1—C7—C8—N1 | −11.3 (3) |
N2—S1—C14—C15 | 80.28 (19) | N1—C9—C10—C11 | −63.9 (2) |
C9—N1—C8—C7 | 176.94 (18) | C9—C10—C11—C12 | −99.8 (2) |
C9—N1—C8—O8 | −3.6 (3) | C9—C10—C11—C16 | 80.1 (2) |
C8—N1—C9—C10 | −87.8 (2) | C10—C11—C12—C13 | −177.48 (19) |
C2—C1—C6—C5 | 1.0 (3) | C16—C11—C12—C13 | 2.6 (3) |
C6—C1—C2—C3 | −0.9 (3) | C10—C11—C16—C15 | 177.60 (19) |
C7—C1—C2—C3 | 178.13 (19) | C12—C11—C16—C15 | −2.5 (3) |
C6—C1—C7—C8 | 90.5 (2) | C11—C12—C13—C14 | −0.2 (3) |
C7—C1—C6—C5 | −177.98 (19) | C12—C13—C14—S1 | 173.52 (16) |
C2—C1—C7—C8 | −88.5 (2) | C12—C13—C14—C15 | −2.4 (3) |
C1—C2—C3—C4 | 0.2 (3) | S1—C14—C15—C16 | −173.42 (16) |
C2—C3—C4—C5 | 0.4 (3) | C13—C14—C15—C16 | 2.5 (3) |
C2—C3—C4—O4 | 178.88 (19) | C14—C15—C16—C11 | 0.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O11i | 0.86 | 2.22 | 2.909 (2) | 138 |
N2—H2A···O8ii | 0.87 | 2.09 | 2.951 (2) | 174 |
N2—H2B···O4iii | 0.87 | 2.19 | 3.001 (3) | 155 |
O4—H4···O8iv | 0.86 | 1.86 | 2.698 (2) | 165 |
C9—H9A···O4v | 0.95 | 2.55 | 3.438 (3) | 156 |
C13—H13···O11 | 0.95 | 2.56 | 2.932 (3) | 103 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z; (iii) x, y+1, z; (iv) x+1/2, −y−1/2, z+1/2; (v) x−1/2, −y−1/2, z−1/2. |
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