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Singly, sulfonamide and chalcone are well known pharmacophoric groups which have several pharmaceutical applications for a variety of diseases. Combination of two or more pharmacophoric groups can enhance the probability of discovering new lead compounds, especially if closely related activities are involved. The title compound, C23H21NO4S, was prepared in order to investigate its potential clinical application. It shows an inter­esting mol­ecule that shows a V-shaped mol­ecular structure formed by sulfonamide and chalcone arms. The chalcone group is quasi-planar and the sulfonamide aromatic ring is almost perpendicular to the mean plane of the chalcone. An infinite zigzag chain parallel to the crystallographic axis [001] results from inter­molecular N—H...O hydrogen bonds and keeps the mol­ecules perfectly stacked in this direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029303/bh2110sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029303/bh2110Isup2.hkl
Contains datablock I

CCDC reference: 655603

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.047
  • wR factor = 0.135
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Comment top

Sulfonamide is a pharmacophoric group of over than 30 pharmaceuticals which are in clinical use, with antibacterial, diuretic, oral antidiabetic, HIV protease inhibitory (Supuran et al., 2003) and antimalarial (Petersen, 2004) activities. Many novel sulfonamide derivatives have recently been reported to show carbonic anhydrase inhibitory action, matrix metalloproteinase inhibitory action, endothelin receptor antagonism, antitumoral (Supuran et al., 2003) and antileishmanial (Bhattacharya et al., 2004) activities.

Naturally occurring and synthetic chalcones are known to have a wide range of potential pharmacological activities, such as anti-inflammatory, antibacterial, anticancer, antiviral, antimalarial (Ni et al., 2004), antitrypanosomal, antileishmanial (Lunardi et al., 2003) and nitric oxide inhibitory action (Rojas et al., 2002). A combination of two or more pharmacophoric groups can enhance the discovery probability of new lead compounds, specially if closely related activities are involved. Recently, analogs of sulfonamide chalcone derivatives were synthesized and showed activity against cultured Plasmodium falciparum parasites (Dominguez et al., 2005). In order to investigate of bioactivity of the combined compounds, we have prepared some sulfonamide chalcone derivatives, and in this paper we present the synthesis and X-ray study of (I).

The molecule of (I) shows an angular geometry (Fig. 1) resulting from the structural combination of sulfonamide and chalcone moieties, with the vertices of the molecule occupied by S atom. The chalcone arm is quasi planar, where the dihedral angles between the best planes of the rings C9···C14 and C18···C23 is 10.85 (6)° and the best plane of the central chain C13—C15 C16—C17 with respect to phenyl rings C9···C14 and C18···C23 are 10.4 (1)° and 11.6 (1)°, respectively. This feature suggests that there is electronic delocalization forming an extended π -electron conjugated system in this moiety. It is in accord with decreased length of the C16—C17 [1.471 (3) Å] single bond and the increased length of the C15C16 [1.322 (4) Å] double bond. In addition, the methoxy group is also almost coplanar with its attached phenyl ring. It was observed in similar structures of chalcone (Subbiah Pandi et al., 2003 and cited references) when the mehtoxy is in para position with respect to the central chain. In the sulfonamide moiety, the distances and angles around N1 and C2 are within the expected range found in similar structures searched in CSD V5.28 with Mogul (Bruno et al., 2004). The phenyl ring C3···C8 is almost perpendicular to the mean plane of the chalcone arm, where the dihedral angle between these planes is 85.04 (8)°. An intermolecular hydrogen bond [N1—H1···O171i, NH = 0.84 (3) Å, H···O = 2.23 (3) Å, N—H···O = 156 (3)°, symmetry code: (i) x, y, z - 1] promotes a zigzag infinite chain formation running parallel to the crystallographic [001] axis (Fig. 2), keeping the molecules stacked in this direction.

Related literature top

For related literature, see: Bhattacharya et al. (2004); Cremlyn et al. (1984); Dominguez et al. (2005); Lunardi et al. (2003); Ni et al. (2004); Subbiah Pandi et al. (2003); Petersen (2004); Rojas et al. (2002); Supuran et al. (2003); Bruno et al. (2004).

Experimental top

Compound (I) was synthesized according to the method of Cremlyn et al. (1984). 4-methoxychalcone (6.63 g, 27.87 mmol), was reacted with chlorosulphonic acid (19.48 g, 167.2 mmol) at room temperature for 1 week. The red solution was poured onto crushed ice with stirring to give the sulfonyl chloride as a yellow solid. The sulfonyl chloride (0.50 g, 1.48 mmol) was treated with benzylamine (0.23 g, 2.19 mmol) in methanol at 273 K. The mixture was reacted at room temperature for 1 h and was then poured onto ice-water. The precipitate was collected by filtration, washed with cold methanol, dried and recrystallized in hot ethanol (yield 0.25 g, 42%). M.p. 167–170°C (yellow crystalline solid). Colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform solution. 1H NMR (CDCl3): δ: 3.89 (s, 3H, OCH3), 4.17 (d, J=6.19 Hz, 2H, CH2), 6.92–8.28 (m, 13H, ArH, 2H olefinic H). Elemental Analysis calculated for C23H21NO4S: C 67.79, H 5.19, N 3.44, S 7.87%; Found: C 67.52, H 5.11, N 3.50, S 7.62%.

Refinement top

All non-H atoms were refined with anisotropic displacement parameters. H atoms attached to C atoms were added at their calculated positions and included in the refinement, with constrained distances C—H = 0.96 (CH3), 0.97 (CH2) or 0.93 Å (CHAr), and Uiso(H) = 1.2Ueq(carrier C) or 1.5Ueq(C102) for the methyl group. Atom H1 bonded to N1 was found in a difference map and treated as an isotropic free atom.

Structure description top

Sulfonamide is a pharmacophoric group of over than 30 pharmaceuticals which are in clinical use, with antibacterial, diuretic, oral antidiabetic, HIV protease inhibitory (Supuran et al., 2003) and antimalarial (Petersen, 2004) activities. Many novel sulfonamide derivatives have recently been reported to show carbonic anhydrase inhibitory action, matrix metalloproteinase inhibitory action, endothelin receptor antagonism, antitumoral (Supuran et al., 2003) and antileishmanial (Bhattacharya et al., 2004) activities.

Naturally occurring and synthetic chalcones are known to have a wide range of potential pharmacological activities, such as anti-inflammatory, antibacterial, anticancer, antiviral, antimalarial (Ni et al., 2004), antitrypanosomal, antileishmanial (Lunardi et al., 2003) and nitric oxide inhibitory action (Rojas et al., 2002). A combination of two or more pharmacophoric groups can enhance the discovery probability of new lead compounds, specially if closely related activities are involved. Recently, analogs of sulfonamide chalcone derivatives were synthesized and showed activity against cultured Plasmodium falciparum parasites (Dominguez et al., 2005). In order to investigate of bioactivity of the combined compounds, we have prepared some sulfonamide chalcone derivatives, and in this paper we present the synthesis and X-ray study of (I).

The molecule of (I) shows an angular geometry (Fig. 1) resulting from the structural combination of sulfonamide and chalcone moieties, with the vertices of the molecule occupied by S atom. The chalcone arm is quasi planar, where the dihedral angles between the best planes of the rings C9···C14 and C18···C23 is 10.85 (6)° and the best plane of the central chain C13—C15 C16—C17 with respect to phenyl rings C9···C14 and C18···C23 are 10.4 (1)° and 11.6 (1)°, respectively. This feature suggests that there is electronic delocalization forming an extended π -electron conjugated system in this moiety. It is in accord with decreased length of the C16—C17 [1.471 (3) Å] single bond and the increased length of the C15C16 [1.322 (4) Å] double bond. In addition, the methoxy group is also almost coplanar with its attached phenyl ring. It was observed in similar structures of chalcone (Subbiah Pandi et al., 2003 and cited references) when the mehtoxy is in para position with respect to the central chain. In the sulfonamide moiety, the distances and angles around N1 and C2 are within the expected range found in similar structures searched in CSD V5.28 with Mogul (Bruno et al., 2004). The phenyl ring C3···C8 is almost perpendicular to the mean plane of the chalcone arm, where the dihedral angle between these planes is 85.04 (8)°. An intermolecular hydrogen bond [N1—H1···O171i, NH = 0.84 (3) Å, H···O = 2.23 (3) Å, N—H···O = 156 (3)°, symmetry code: (i) x, y, z - 1] promotes a zigzag infinite chain formation running parallel to the crystallographic [001] axis (Fig. 2), keeping the molecules stacked in this direction.

For related literature, see: Bhattacharya et al. (2004); Cremlyn et al. (1984); Dominguez et al. (2005); Lunardi et al. (2003); Ni et al. (2004); Subbiah Pandi et al. (2003); Petersen (2004); Rojas et al. (2002); Supuran et al. (2003); Bruno et al. (2004).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
[Figure 2] Fig. 2. Packing of (I) showing the molecules connected through hydrogen bonds and stacked along [001].
5-(2-Benzoylethenyl)-N-benzyl-2-methoxybenzenesulfonamide top
Crystal data top
C23H21NO4SF(000) = 428
Mr = 407.47Dx = 1.379 Mg m3
Triclinic, P1Melting point = 440–443 K
a = 10.3671 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3750 (8) ÅCell parameters from 25 reflections
c = 10.7977 (14) Åθ = 6.7–15.4°
α = 84.88 (1)°µ = 0.20 mm1
β = 68.79 (1)°T = 293 K
γ = 65.40 (1)°Irregular block, colourless
V = 981.9 (2) Å30.50 × 0.33 × 0.13 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
2573 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.1°, θmin = 2.0°
ω–2θ scansh = 1211
Absorption correction: ψ scan
(PLATON; Spek, 2003; North et al., 1968)
k = 1212
Tmin = 0.924, Tmax = 0.969l = 120
3694 measured reflections3 standard reflections every 200 reflections
3490 independent reflections intensity decay: <1%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.067P)2 + 0.4657P]
where P = (Fo2 + 2Fc2)/3
3490 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
C23H21NO4Sγ = 65.40 (1)°
Mr = 407.47V = 981.9 (2) Å3
Triclinic, P1Z = 2
a = 10.3671 (12) ÅMo Kα radiation
b = 10.3750 (8) ŵ = 0.20 mm1
c = 10.7977 (14) ÅT = 293 K
α = 84.88 (1)°0.50 × 0.33 × 0.13 mm
β = 68.79 (1)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2573 reflections with I > 2σ(I)
Absorption correction: ψ scan
(PLATON; Spek, 2003; North et al., 1968)
Rint = 0.027
Tmin = 0.924, Tmax = 0.9693 standard reflections every 200 reflections
3694 measured reflections intensity decay: <1%
3490 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.35 e Å3
3490 reflectionsΔρmin = 0.47 e Å3
266 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.28300 (8)0.31669 (7)0.78462 (6)0.0353 (2)
O10.2332 (2)0.43617 (19)0.87332 (18)0.0461 (5)
O20.4138 (2)0.2877 (2)0.66670 (18)0.0484 (5)
N10.1427 (3)0.3383 (2)0.7393 (2)0.0367 (5)
H10.170 (3)0.275 (3)0.681 (3)0.044 (8)*
C20.0055 (3)0.3700 (3)0.8446 (3)0.0480 (7)
H2A0.02650.44460.90660.058*
H2B0.00140.28590.89320.058*
C30.1333 (3)0.4163 (3)0.7925 (3)0.0420 (7)
C40.2592 (4)0.3912 (4)0.8631 (3)0.0589 (9)
H40.26330.34500.94140.071*
C50.3807 (4)0.4334 (4)0.8197 (4)0.0693 (10)
H50.46560.41620.86890.083*
C60.3745 (4)0.5010 (4)0.7030 (4)0.0654 (10)
H60.45450.52810.67230.079*
C70.2501 (4)0.5281 (3)0.6327 (3)0.0604 (9)
H70.24660.57520.55490.073*
C80.1298 (4)0.4863 (3)0.6762 (3)0.0489 (7)
H80.04580.50500.62730.059*
C90.3096 (3)0.1678 (3)0.8821 (2)0.0315 (6)
C100.3649 (3)0.0305 (3)0.8251 (2)0.0325 (6)
C110.3815 (3)0.0826 (3)0.9063 (3)0.0380 (6)
H110.41920.17470.86980.046*
C120.3421 (3)0.0579 (3)1.0408 (3)0.0381 (6)
H120.35340.13471.09390.046*
C130.2860 (3)0.0776 (3)1.1006 (2)0.0345 (6)
C140.2715 (3)0.1896 (3)1.0186 (2)0.0331 (6)
H140.23550.28121.05550.040*
C150.2394 (3)0.1059 (3)1.2440 (2)0.0376 (6)
H150.21340.19801.27340.045*
C160.2302 (3)0.0138 (3)1.3362 (2)0.0393 (6)
H160.25760.08001.31020.047*
C170.1780 (3)0.0552 (3)1.4786 (2)0.0362 (6)
C180.1533 (3)0.0500 (3)1.5782 (2)0.0348 (6)
C190.2058 (4)0.1925 (3)1.5438 (3)0.0468 (7)
H190.25170.22551.45450.056*
C200.1905 (4)0.2867 (3)1.6415 (3)0.0562 (9)
H200.22590.38281.61770.067*
C210.1231 (4)0.2384 (3)1.7735 (3)0.0519 (8)
H210.11440.30201.83910.062*
C220.0689 (3)0.0973 (3)1.8085 (3)0.0477 (7)
H220.02220.06481.89800.057*
C230.0829 (3)0.0028 (3)1.7121 (3)0.0407 (6)
H230.04490.09341.73670.049*
C1020.4726 (3)0.1232 (3)0.6292 (3)0.0449 (7)
H10A0.48820.11770.53600.067*
H10B0.41160.17530.66870.067*
H10C0.56910.17080.64020.067*
O1010.3966 (2)0.01728 (18)0.69291 (16)0.0388 (5)
O1710.1559 (3)0.1728 (2)1.51546 (18)0.0480 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0476 (4)0.0353 (4)0.0232 (3)0.0175 (3)0.0134 (3)0.0062 (2)
O10.0728 (14)0.0373 (10)0.0336 (10)0.0245 (10)0.0239 (10)0.0065 (8)
O20.0534 (13)0.0578 (12)0.0324 (11)0.0282 (10)0.0082 (9)0.0077 (9)
N10.0428 (13)0.0399 (12)0.0222 (11)0.0095 (10)0.0143 (10)0.0004 (9)
C20.0459 (17)0.0610 (19)0.0276 (14)0.0138 (14)0.0123 (13)0.0011 (13)
C30.0463 (17)0.0397 (15)0.0357 (15)0.0113 (13)0.0170 (13)0.0008 (12)
C40.062 (2)0.065 (2)0.052 (2)0.0281 (18)0.0229 (17)0.0136 (16)
C50.054 (2)0.068 (2)0.089 (3)0.0280 (18)0.026 (2)0.008 (2)
C60.062 (2)0.058 (2)0.079 (3)0.0098 (17)0.044 (2)0.0065 (18)
C70.064 (2)0.058 (2)0.054 (2)0.0100 (17)0.0330 (18)0.0060 (15)
C80.0480 (18)0.0538 (18)0.0383 (16)0.0127 (14)0.0186 (14)0.0050 (13)
C90.0362 (14)0.0368 (13)0.0234 (12)0.0145 (11)0.0143 (11)0.0066 (10)
C100.0336 (14)0.0394 (14)0.0244 (13)0.0138 (11)0.0120 (11)0.0036 (10)
C110.0499 (17)0.0345 (14)0.0293 (14)0.0155 (12)0.0166 (12)0.0043 (11)
C120.0494 (16)0.0380 (14)0.0289 (14)0.0186 (13)0.0179 (12)0.0115 (11)
C130.0379 (15)0.0429 (14)0.0255 (13)0.0189 (12)0.0130 (11)0.0072 (11)
C140.0394 (15)0.0345 (13)0.0252 (13)0.0138 (11)0.0133 (11)0.0026 (10)
C150.0459 (16)0.0452 (15)0.0260 (13)0.0200 (13)0.0167 (12)0.0047 (11)
C160.0535 (17)0.0423 (15)0.0241 (13)0.0208 (13)0.0157 (12)0.0054 (11)
C170.0444 (16)0.0420 (15)0.0262 (13)0.0195 (13)0.0159 (12)0.0057 (11)
C180.0384 (15)0.0445 (15)0.0243 (13)0.0179 (12)0.0138 (11)0.0045 (11)
C190.065 (2)0.0474 (16)0.0289 (15)0.0258 (15)0.0159 (14)0.0046 (12)
C200.082 (2)0.0429 (17)0.0404 (17)0.0256 (16)0.0196 (17)0.0082 (13)
C210.067 (2)0.0583 (19)0.0350 (16)0.0330 (17)0.0186 (15)0.0178 (14)
C220.0548 (19)0.065 (2)0.0235 (14)0.0287 (16)0.0106 (13)0.0070 (13)
C230.0480 (17)0.0463 (16)0.0287 (14)0.0208 (13)0.0130 (13)0.0023 (11)
C1020.0517 (18)0.0476 (16)0.0296 (14)0.0157 (14)0.0125 (13)0.0044 (12)
O1010.0537 (12)0.0380 (10)0.0212 (9)0.0140 (9)0.0151 (8)0.0005 (7)
O1710.0739 (14)0.0467 (12)0.0284 (10)0.0295 (10)0.0194 (10)0.0076 (8)
Geometric parameters (Å, º) top
S1—O21.425 (2)C12—C131.392 (4)
S1—O11.4280 (19)C12—H120.9300
S1—N11.621 (2)C13—C141.386 (3)
S1—C91.770 (2)C13—C151.462 (3)
N1—C21.464 (4)C14—H140.9300
N1—H10.84 (3)C15—C161.322 (4)
C2—C31.505 (4)C15—H150.9300
C2—H2A0.9700C16—C171.471 (3)
C2—H2B0.9700C16—H160.9300
C3—C41.371 (4)C17—O1711.219 (3)
C3—C81.390 (4)C17—C181.496 (4)
C4—C51.389 (5)C18—C191.378 (4)
C4—H40.9300C18—C231.388 (3)
C5—C61.380 (5)C19—C201.384 (4)
C5—H50.9300C19—H190.9300
C6—C71.369 (5)C20—C211.374 (4)
C6—H60.9300C20—H200.9300
C7—C81.378 (4)C21—C221.364 (4)
C7—H70.9300C21—H210.9300
C8—H80.9300C22—C231.375 (4)
C9—C141.394 (3)C22—H220.9300
C9—C101.398 (3)C23—H230.9300
C10—O1011.350 (3)C102—O1011.430 (3)
C10—C111.390 (3)C102—H10A0.9600
C11—C121.376 (4)C102—H10B0.9600
C11—H110.9300C102—H10C0.9600
O2—S1—O1119.04 (12)C11—C12—H12118.7
O2—S1—N1107.38 (12)C13—C12—H12118.7
O1—S1—N1107.21 (12)C14—C13—C12117.3 (2)
O2—S1—C9110.21 (12)C14—C13—C15119.6 (2)
O1—S1—C9105.83 (11)C12—C13—C15123.0 (2)
N1—S1—C9106.50 (12)C13—C14—C9121.4 (2)
C2—N1—S1117.40 (18)C13—C14—H14119.3
C2—N1—H1115 (2)C9—C14—H14119.3
S1—N1—H1110 (2)C16—C15—C13126.7 (3)
N1—C2—C3113.2 (2)C16—C15—H15116.7
N1—C2—H2A108.9C13—C15—H15116.7
C3—C2—H2A108.9C15—C16—C17121.9 (3)
N1—C2—H2B108.9C15—C16—H16119.0
C3—C2—H2B108.9C17—C16—H16119.0
H2A—C2—H2B107.8O171—C17—C16120.9 (2)
C4—C3—C8118.5 (3)O171—C17—C18120.2 (2)
C4—C3—C2119.1 (3)C16—C17—C18118.9 (2)
C8—C3—C2122.3 (3)C19—C18—C23118.8 (2)
C3—C4—C5121.2 (3)C19—C18—C17123.1 (2)
C3—C4—H4119.4C23—C18—C17118.0 (2)
C5—C4—H4119.4C18—C19—C20120.4 (3)
C6—C5—C4119.5 (3)C18—C19—H19119.8
C6—C5—H5120.2C20—C19—H19119.8
C4—C5—H5120.2C21—C20—C19120.0 (3)
C7—C6—C5119.7 (3)C21—C20—H20120.0
C7—C6—H6120.2C19—C20—H20120.0
C5—C6—H6120.2C22—C21—C20120.1 (3)
C6—C7—C8120.6 (3)C22—C21—H21119.9
C6—C7—H7119.7C20—C21—H21119.9
C8—C7—H7119.7C21—C22—C23120.3 (3)
C7—C8—C3120.4 (3)C21—C22—H22119.9
C7—C8—H8119.8C23—C22—H22119.9
C3—C8—H8119.8C22—C23—C18120.4 (3)
C14—C9—C10119.9 (2)C22—C23—H23119.8
C14—C9—S1118.77 (19)C18—C23—H23119.8
C10—C9—S1121.27 (18)O101—C102—H10A109.5
O101—C10—C11124.1 (2)O101—C102—H10B109.5
O101—C10—C9116.9 (2)H10A—C102—H10B109.5
C11—C10—C9119.0 (2)O101—C102—H10C109.5
C12—C11—C10119.8 (2)H10A—C102—H10C109.5
C12—C11—H11120.1H10B—C102—H10C109.5
C10—C11—H11120.1C10—O101—C102117.8 (2)
C11—C12—C13122.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O171i0.84 (3)2.23 (3)3.018 (3)156 (3)
Symmetry code: (i) x, y, z1.

Experimental details

Crystal data
Chemical formulaC23H21NO4S
Mr407.47
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.3671 (12), 10.3750 (8), 10.7977 (14)
α, β, γ (°)84.88 (1), 68.79 (1), 65.40 (1)
V3)981.9 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.50 × 0.33 × 0.13
Data collection
DiffractometerEnraf-Nonius CAD-4
Absorption correctionψ scan
(PLATON; Spek, 2003; North et al., 1968)
Tmin, Tmax0.924, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
3694, 3490, 2573
Rint0.027
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.135, 1.05
No. of reflections3490
No. of parameters266
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.47

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O171i0.84 (3)2.23 (3)3.018 (3)156 (3)
Symmetry code: (i) x, y, z1.
 

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