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The crystal structure of the title sulfonamide, C16H18N2O4S, is stabilized by strong N—H...O and O—H...O inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051348/hb2220sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051348/hb2220Isup2.hkl
Contains datablock I

CCDC reference: 633863

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C16H18N2O4SF(000) = 704
Mr = 334.39Dx = 1.405 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 15.715 (3) Åθ = 12.8–17.2°
b = 10.250 (2) ŵ = 0.23 mm1
c = 9.819 (3) ÅT = 295 K
β = 91.862 (18)°Prism, colorless
V = 1580.8 (6) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.037
Radiation source: Rigaku rotating anodeθmax = 25.0°, θmin = 2.6°
Graphite monochromatorh = 1818
ω–2θ scansk = 012
3219 measured reflectionsl = 115
2779 independent reflections3 standard reflections every 150 reflections
2100 reflections with I > 2σ(I) intensity decay: 0.8%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.37 e Å3
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 &gt; 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
xyzUiso*/Ueq
S10.15036 (3)0.16214 (6)0.45805 (5)0.0412 (2)
O40.12798 (10)0.44728 (16)0.39567 (16)0.0494 (5)
O80.22426 (9)0.18689 (15)0.09475 (14)0.0451 (5)
O110.13205 (11)0.21505 (19)0.58883 (14)0.0564 (6)
O120.20507 (11)0.05214 (17)0.4487 (2)0.0623 (6)
N10.17633 (10)0.17636 (17)0.12408 (16)0.0355 (5)
N20.19320 (11)0.27858 (19)0.37363 (17)0.0420 (6)
C10.05157 (12)0.3702 (2)0.08473 (19)0.0338 (6)
C20.02723 (14)0.3102 (2)0.0851 (2)0.0423 (7)
C30.08824 (13)0.3331 (2)0.1876 (2)0.0436 (7)
C40.07026 (12)0.4176 (2)0.2912 (2)0.0357 (6)
C50.00737 (13)0.4800 (2)0.2933 (2)0.0426 (7)
C60.06737 (13)0.4556 (2)0.1892 (2)0.0429 (7)
C70.11813 (14)0.3411 (2)0.0252 (2)0.0423 (7)
C80.17668 (12)0.2283 (2)0.00006 (19)0.0335 (6)
C90.22572 (13)0.0639 (2)0.1634 (2)0.0405 (7)
C100.18061 (15)0.0649 (2)0.1401 (2)0.0509 (8)
C110.09913 (14)0.0831 (2)0.2251 (2)0.0401 (7)
C120.09757 (14)0.1574 (2)0.3431 (2)0.0465 (8)
C130.02252 (14)0.1782 (2)0.4179 (2)0.0447 (7)
C140.05229 (13)0.1235 (2)0.3745 (2)0.0360 (6)
C150.05157 (14)0.0448 (2)0.2602 (2)0.0439 (7)
C160.02385 (15)0.0254 (2)0.1868 (2)0.0459 (7)
H10.144300.212200.185700.0400*
H20.039500.251200.013500.0480*
H2A0.198400.253500.290100.0500*
H2B0.159300.345400.373700.0500*
H30.142100.291500.184900.0500*
H40.174800.405900.383600.0540*
H50.020000.538100.365700.0480*
H60.120500.499600.189800.0480*
H7A0.089300.324400.107700.0480*
H7B0.152300.417600.037700.0480*
H9A0.278000.063300.111500.0460*
H9B0.237600.071000.257600.0460*
H10A0.167300.070700.047200.0570*
H10B0.218300.134000.162700.0570*
H120.149300.194500.373600.0530*
H130.022500.229500.498900.0510*
H150.102600.003900.232400.0500*
H160.024700.028600.107400.0520*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0421 (3)0.0505 (4)0.0304 (3)0.0041 (3)0.0091 (2)0.0032 (2)
O40.0431 (9)0.0567 (10)0.0473 (9)0.0056 (8)0.0174 (7)0.0110 (8)
O80.0431 (8)0.0640 (10)0.0274 (7)0.0104 (8)0.0111 (6)0.0017 (7)
O110.0604 (10)0.0844 (13)0.0237 (7)0.0005 (9)0.0088 (7)0.0011 (8)
O120.0535 (10)0.0580 (11)0.0745 (12)0.0169 (9)0.0133 (9)0.0058 (10)
N10.0327 (9)0.0468 (10)0.0262 (8)0.0058 (8)0.0096 (7)0.0033 (7)
N20.0409 (10)0.0525 (11)0.0322 (9)0.0001 (9)0.0067 (8)0.0013 (8)
C10.0300 (10)0.0405 (11)0.0307 (10)0.0033 (9)0.0028 (8)0.0045 (9)
C20.0395 (12)0.0469 (13)0.0403 (12)0.0022 (10)0.0004 (9)0.0118 (10)
C30.0312 (11)0.0465 (13)0.0525 (13)0.0055 (10)0.0055 (9)0.0084 (11)
C40.0345 (10)0.0387 (12)0.0335 (11)0.0017 (9)0.0069 (8)0.0005 (9)
C50.0411 (12)0.0505 (14)0.0361 (12)0.0063 (10)0.0014 (9)0.0117 (10)
C60.0316 (11)0.0517 (14)0.0452 (13)0.0082 (10)0.0005 (9)0.0002 (11)
C70.0421 (12)0.0529 (13)0.0312 (11)0.0046 (10)0.0076 (9)0.0052 (10)
C80.0280 (9)0.0455 (12)0.0267 (10)0.0023 (9)0.0051 (8)0.0004 (9)
C90.0331 (11)0.0563 (14)0.0315 (11)0.0073 (10)0.0102 (8)0.0078 (10)
C100.0548 (14)0.0478 (14)0.0489 (14)0.0088 (11)0.0182 (11)0.0004 (11)
C110.0460 (12)0.0339 (11)0.0397 (11)0.0008 (10)0.0088 (9)0.0031 (9)
C120.0406 (12)0.0444 (13)0.0540 (14)0.0097 (10)0.0049 (10)0.0096 (11)
C130.0461 (13)0.0478 (13)0.0399 (12)0.0058 (11)0.0024 (10)0.0136 (10)
C140.0390 (11)0.0371 (11)0.0315 (10)0.0002 (9)0.0036 (8)0.0007 (9)
C150.0419 (12)0.0486 (13)0.0415 (12)0.0001 (10)0.0042 (10)0.0079 (10)
C160.0530 (14)0.0502 (13)0.0345 (11)0.0068 (11)0.0017 (10)0.0105 (10)
Geometric parameters (Å, º) top
S1—O111.4318 (16)C10—C111.517 (3)
S1—O121.4227 (19)C11—C121.386 (3)
S1—N21.613 (2)C11—C161.386 (3)
S1—C141.767 (2)C12—C131.386 (3)
O4—C41.381 (3)C13—C141.382 (3)
O8—C81.249 (2)C14—C151.382 (3)
O4—H40.8600C15—C161.381 (3)
N1—C91.449 (3)C2—H20.9500
N1—C81.329 (3)C3—H30.9500
N1—H10.8600C5—H50.9500
N2—H2A0.8700C6—H60.9500
N2—H2B0.8700C7—H7A0.9600
C1—C21.383 (3)C7—H7B0.9600
C1—C61.377 (3)C9—H9A0.9500
C1—C71.508 (3)C9—H9B0.9500
C2—C31.387 (3)C10—H10A0.9400
C3—C41.372 (3)C10—H10B0.9500
C4—C51.378 (3)C12—H120.9500
C5—C61.391 (3)C13—H130.9500
C7—C81.503 (3)C15—H150.9500
C9—C101.519 (3)C16—H160.9600
O11—S1—O12119.84 (11)S1—C14—C15119.46 (16)
O11—S1—N2106.27 (11)C13—C14—C15120.17 (19)
O11—S1—C14107.67 (10)C14—C15—C16119.5 (2)
O12—S1—N2106.86 (10)C11—C16—C15121.51 (19)
O12—S1—C14108.19 (11)C1—C2—H2119.00
N2—S1—C14107.43 (9)C3—C2—H2119.00
C4—O4—H4109.00C2—C3—H3120.00
C8—N1—C9125.21 (17)C4—C3—H3121.00
C9—N1—H1117.00C4—C5—H5120.00
C8—N1—H1117.00C6—C5—H5121.00
H2A—N2—H2B108.00C1—C6—H6119.00
S1—N2—H2B108.00C5—C6—H6119.00
S1—N2—H2A109.00C1—C7—H7A108.00
C6—C1—C7121.41 (18)C1—C7—H7B108.00
C2—C1—C6117.64 (18)C8—C7—H7A108.00
C2—C1—C7120.94 (18)C8—C7—H7B108.00
C1—C2—C3121.63 (19)H7A—C7—H7B109.00
C2—C3—C4119.37 (19)N1—C9—H9A109.00
O4—C4—C5116.55 (18)N1—C9—H9B109.00
O4—C4—C3122.92 (18)C10—C9—H9A108.00
C3—C4—C5120.51 (18)C10—C9—H9B109.00
C4—C5—C6119.01 (19)H9A—C9—H9B109.00
C1—C6—C5121.83 (19)C9—C10—H10A109.00
C1—C7—C8116.62 (17)C9—C10—H10B108.00
O8—C8—C7119.55 (17)C11—C10—H10A108.00
N1—C8—C7118.36 (17)C11—C10—H10B107.00
O8—C8—N1122.09 (18)H10A—C10—H10B110.00
N1—C9—C10113.24 (17)C11—C12—H12119.00
C9—C10—C11114.43 (17)C13—C12—H12119.00
C12—C11—C16118.0 (2)C12—C13—H13120.00
C10—C11—C16120.73 (18)C14—C13—H13120.00
C10—C11—C12121.27 (19)C14—C15—H15120.00
C11—C12—C13121.3 (2)C16—C15—H15120.00
C12—C13—C14119.48 (19)C11—C16—H16119.00
S1—C14—C13120.24 (16)C15—C16—H16120.00
O11—S1—C14—C1318.5 (2)C3—C4—C5—C60.3 (3)
O11—S1—C14—C15165.63 (17)O4—C4—C5—C6178.84 (18)
O12—S1—C14—C13149.33 (17)C4—C5—C6—C10.5 (3)
O12—S1—C14—C1534.8 (2)C1—C7—C8—O8169.19 (18)
N2—S1—C14—C1395.63 (18)C1—C7—C8—N111.3 (3)
N2—S1—C14—C1580.28 (19)N1—C9—C10—C1163.9 (2)
C9—N1—C8—C7176.94 (18)C9—C10—C11—C1299.8 (2)
C9—N1—C8—O83.6 (3)C9—C10—C11—C1680.1 (2)
C8—N1—C9—C1087.8 (2)C10—C11—C12—C13177.48 (19)
C2—C1—C6—C51.0 (3)C16—C11—C12—C132.6 (3)
C6—C1—C2—C30.9 (3)C10—C11—C16—C15177.60 (19)
C7—C1—C2—C3178.13 (19)C12—C11—C16—C152.5 (3)
C6—C1—C7—C890.5 (2)C11—C12—C13—C140.2 (3)
C7—C1—C6—C5177.98 (19)C12—C13—C14—S1173.52 (16)
C2—C1—C7—C888.5 (2)C12—C13—C14—C152.4 (3)
C1—C2—C3—C40.2 (3)S1—C14—C15—C16173.42 (16)
C2—C3—C4—C50.4 (3)C13—C14—C15—C162.5 (3)
C2—C3—C4—O4178.88 (19)C14—C15—C16—C110.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O11i0.862.222.909 (2)138
N2—H2A···O8ii0.872.092.951 (2)174
N2—H2B···O4iii0.872.193.001 (3)155
O4—H4···O8iv0.861.862.698 (2)165
C9—H9A···O4v0.952.553.438 (3)156
C13—H13···O110.952.562.932 (3)103
Symmetry codes: (i) x, y, z+1; (ii) x, y, z; (iii) x, y+1, z; (iv) x+1/2, y1/2, z+1/2; (v) x1/2, y1/2, z1/2.
 

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