organic compounds
Gliquidone
aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
*Correspondence e-mail: thomas.gelbrich@uibk.ac.at
The title compound {systematic name: N-cyclohexylcarbamoyl-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide}, C27H33N3O6S, displays an intramolecular N—H⋯O=S interaction, as well as intermolecular N—H⋯O=C hydrogen bonds. The latter interactions lead to the formation of hydrogen-bonded chains parallel to the c axis. The conformation of the sulfonylurea fragment is in agreement with a recent theoretical study [Kasetti et al. (2010). J. Phys. Chem. B, 114, 11603–11610].
Related literature
For theoretical studies of the molecular structure, see Lins et al. (1996); Kasetti et al. (2010). For thermomicroscopy, see Kuhnert-Brandstätter et al. (1982). For related crystal structures, see: Kobelt & Paulus (1972); Iwata et al. (1997); Grell et al. (1998); Endo et al. (2003).
Experimental
Crystal data
|
Refinement
|
Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536811016680/jh2285sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811016680/jh2285Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811016680/jh2285Isup3.cml
All H atoms were identified in a difference map. Methyl H atoms were idealized and included as rigid groups allowed to rotate but not tip (C—H = 0.98 Å). H atoms in CH2 (C—H = 0.99 Å) or CH (C—H = 1.00 Å) groups and H atoms bonded to aromatic carbon atoms (C—H = 0.95 Å) were positioned geometrically. Hydrogen atoms attached to N were refined with restrained distances [N—H = 0.88 (2) Å]. Uĩso parameters for all H atoms were refined freely.
Data collection: COLLECT (Hooft, 1998); cell
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C27H33N3O6S | F(000) = 1120 |
Mr = 527.62 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 16476 reflections |
a = 19.1494 (4) Å | θ = 2.9–27.5° |
b = 10.7253 (3) Å | µ = 0.17 mm−1 |
c = 13.8024 (2) Å | T = 120 K |
β = 106.691 (1)° | Plate, colourless |
V = 2715.34 (10) Å3 | 0.40 × 0.40 × 0.10 mm |
Z = 4 |
Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer | 5325 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 4361 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 9.091 pixels mm-1 | θmax = 26.0°, θmin = 2.9° |
ϕ and ω scans | h = −23→23 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | k = −13→13 |
Tmin = 0.937, Tmax = 0.984 | l = −15→17 |
28737 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.7288P] where P = (Fo2 + 2Fc2)/3 |
5325 reflections | (Δ/σ)max = 0.001 |
376 parameters | Δρmax = 0.28 e Å−3 |
2 restraints | Δρmin = −0.43 e Å−3 |
C27H33N3O6S | V = 2715.34 (10) Å3 |
Mr = 527.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.1494 (4) Å | µ = 0.17 mm−1 |
b = 10.7253 (3) Å | T = 120 K |
c = 13.8024 (2) Å | 0.40 × 0.40 × 0.10 mm |
β = 106.691 (1)° |
Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer | 5325 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 4361 reflections with I > 2σ(I) |
Tmin = 0.937, Tmax = 0.984 | Rint = 0.044 |
28737 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 2 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.28 e Å−3 |
5325 reflections | Δρmin = −0.43 e Å−3 |
376 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.372978 (18) | 0.06096 (4) | 0.34758 (2) | 0.02071 (11) | |
O1 | 0.44637 (5) | 0.05111 (11) | 0.41217 (7) | 0.0251 (2) | |
O2 | 0.35950 (6) | 0.06083 (11) | 0.24022 (7) | 0.0291 (3) | |
O3 | 0.26601 (6) | −0.14284 (11) | 0.47583 (8) | 0.0301 (3) | |
O4 | 0.04953 (6) | 0.56657 (10) | 0.38426 (7) | 0.0264 (3) | |
O5 | 0.19863 (6) | 0.53754 (12) | 0.70230 (8) | 0.0384 (3) | |
O6 | −0.15069 (6) | 0.85561 (11) | 0.38996 (8) | 0.0306 (3) | |
N1 | 0.32644 (7) | −0.05733 (12) | 0.37222 (9) | 0.0229 (3) | |
H1N | 0.2868 (9) | −0.0629 (18) | 0.3241 (13) | 0.040 (5)* | |
N2 | 0.38277 (7) | −0.07655 (13) | 0.54610 (9) | 0.0251 (3) | |
H2N | 0.4223 (8) | −0.0513 (17) | 0.5327 (13) | 0.031 (5)* | |
N3 | 0.12334 (6) | 0.55263 (11) | 0.54472 (8) | 0.0190 (3) | |
C1 | 0.33329 (7) | 0.19457 (14) | 0.38350 (10) | 0.0189 (3) | |
C2 | 0.36549 (8) | 0.24940 (15) | 0.47723 (10) | 0.0216 (3) | |
H2 | 0.4099 | 0.2175 | 0.5203 | 0.027 (4)* | |
C3 | 0.33191 (8) | 0.35119 (15) | 0.50681 (10) | 0.0225 (3) | |
H3 | 0.3534 | 0.3886 | 0.5709 | 0.034 (5)* | |
C4 | 0.26712 (8) | 0.39936 (14) | 0.44388 (11) | 0.0217 (3) | |
C5 | 0.23624 (8) | 0.34344 (15) | 0.35000 (11) | 0.0244 (3) | |
H5 | 0.1922 | 0.3760 | 0.3065 | 0.031 (5)* | |
C6 | 0.26863 (8) | 0.24152 (15) | 0.31929 (11) | 0.0228 (3) | |
H6 | 0.2471 | 0.2040 | 0.2553 | 0.031 (4)* | |
C7 | 0.22896 (8) | 0.50595 (15) | 0.47875 (11) | 0.0248 (3) | |
H7A | 0.2106 | 0.5662 | 0.4228 | 0.040 (5)* | |
H7B | 0.2635 | 0.5500 | 0.5358 | 0.026 (4)* | |
C8 | 0.16539 (8) | 0.45372 (14) | 0.51243 (11) | 0.0215 (3) | |
H8A | 0.1325 | 0.4065 | 0.4558 | 0.026 (4)* | |
H8B | 0.1845 | 0.3950 | 0.5692 | 0.031 (5)* | |
C9 | 0.06399 (7) | 0.60349 (14) | 0.47150 (10) | 0.0184 (3) | |
C10 | 0.02037 (7) | 0.69887 (13) | 0.50490 (10) | 0.0184 (3) | |
C11 | 0.04048 (8) | 0.74227 (14) | 0.60447 (10) | 0.0214 (3) | |
C12 | 0.10805 (8) | 0.69515 (14) | 0.68274 (10) | 0.0216 (3) | |
C13 | 0.14635 (8) | 0.58977 (15) | 0.64517 (11) | 0.0232 (3) | |
C14 | −0.04261 (7) | 0.74093 (14) | 0.43406 (10) | 0.0204 (3) | |
H14 | −0.0546 | 0.7117 | 0.3663 | 0.026 (4)* | |
C15 | −0.08755 (8) | 0.82517 (15) | 0.46246 (11) | 0.0235 (3) | |
C16 | −0.06813 (9) | 0.87156 (16) | 0.56085 (11) | 0.0301 (4) | |
H16 | −0.0983 | 0.9310 | 0.5803 | 0.038 (5)* | |
C17 | −0.00459 (9) | 0.83075 (16) | 0.63026 (11) | 0.0290 (4) | |
H17 | 0.0086 | 0.8638 | 0.6969 | 0.035 (5)* | |
C18 | 0.16458 (9) | 0.80078 (17) | 0.71456 (13) | 0.0368 (4) | |
H18A | 0.1814 | 0.8253 | 0.6566 | 0.054 (6)* | |
H18B | 0.2061 | 0.7716 | 0.7695 | 0.044 (5)* | |
H18C | 0.1421 | 0.8727 | 0.7378 | 0.042 (5)* | |
C19 | 0.08837 (9) | 0.64511 (17) | 0.77617 (11) | 0.0331 (4) | |
H19A | 0.0675 | 0.7126 | 0.8069 | 0.047 (6)* | |
H19B | 0.1324 | 0.6133 | 0.8254 | 0.039 (5)* | |
H19C | 0.0526 | 0.5776 | 0.7556 | 0.068 (7)* | |
C20 | −0.20530 (9) | 0.91933 (18) | 0.42316 (13) | 0.0369 (4) | |
H20A | −0.2180 | 0.8696 | 0.4752 | 0.042 (5)* | |
H20B | −0.2488 | 0.9314 | 0.3657 | 0.047 (6)* | |
H20C | −0.1865 | 1.0006 | 0.4513 | 0.039 (5)* | |
C21 | 0.32254 (8) | −0.09519 (14) | 0.46937 (11) | 0.0217 (3) | |
C22 | 0.38491 (8) | −0.09235 (15) | 0.65249 (11) | 0.0228 (3) | |
H22 | 0.3337 | −0.1030 | 0.6557 | 0.031 (4)* | |
C23 | 0.42853 (9) | −0.20722 (15) | 0.69978 (12) | 0.0292 (4) | |
H23A | 0.4786 | −0.2015 | 0.6932 | 0.029 (4)* | |
H23B | 0.4053 | −0.2830 | 0.6636 | 0.049 (6)* | |
C24 | 0.43184 (9) | −0.21684 (16) | 0.81155 (12) | 0.0333 (4) | |
H24A | 0.3821 | −0.2302 | 0.8174 | 0.041 (5)* | |
H24B | 0.4619 | −0.2897 | 0.8419 | 0.051 (6)* | |
C25 | 0.46396 (9) | −0.10010 (17) | 0.86938 (12) | 0.0328 (4) | |
H25A | 0.5152 | −0.0906 | 0.8687 | 0.032 (5)* | |
H25B | 0.4636 | −0.1082 | 0.9407 | 0.039 (5)* | |
C26 | 0.42077 (9) | 0.01468 (17) | 0.82278 (12) | 0.0314 (4) | |
H26A | 0.4446 | 0.0901 | 0.8588 | 0.035 (5)* | |
H26B | 0.3710 | 0.0096 | 0.8304 | 0.039 (5)* | |
C27 | 0.41609 (8) | 0.02515 (15) | 0.71081 (11) | 0.0251 (3) | |
H27A | 0.3849 | 0.0972 | 0.6812 | 0.031 (5)* | |
H27B | 0.4654 | 0.0407 | 0.7039 | 0.027 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01746 (19) | 0.0296 (2) | 0.01411 (19) | 0.00384 (15) | 0.00301 (14) | −0.00118 (14) |
O1 | 0.0158 (5) | 0.0382 (7) | 0.0206 (5) | 0.0056 (4) | 0.0038 (4) | 0.0007 (4) |
O2 | 0.0295 (6) | 0.0427 (7) | 0.0148 (5) | 0.0065 (5) | 0.0059 (4) | −0.0014 (5) |
O3 | 0.0242 (6) | 0.0330 (7) | 0.0310 (6) | −0.0057 (5) | 0.0048 (4) | −0.0019 (5) |
O4 | 0.0293 (6) | 0.0314 (6) | 0.0161 (5) | 0.0073 (5) | 0.0026 (4) | −0.0029 (4) |
O5 | 0.0346 (7) | 0.0451 (8) | 0.0252 (6) | 0.0187 (6) | −0.0080 (5) | −0.0040 (5) |
O6 | 0.0235 (6) | 0.0404 (7) | 0.0238 (5) | 0.0148 (5) | 0.0003 (4) | 0.0004 (5) |
N1 | 0.0215 (7) | 0.0252 (7) | 0.0183 (6) | 0.0010 (5) | 0.0000 (5) | −0.0041 (5) |
N2 | 0.0173 (6) | 0.0384 (8) | 0.0185 (6) | 0.0005 (6) | 0.0033 (5) | 0.0028 (5) |
N3 | 0.0191 (6) | 0.0196 (6) | 0.0169 (6) | 0.0035 (5) | 0.0029 (5) | 0.0004 (5) |
C1 | 0.0166 (7) | 0.0237 (8) | 0.0166 (7) | −0.0004 (6) | 0.0054 (5) | 0.0004 (6) |
C2 | 0.0157 (7) | 0.0307 (8) | 0.0164 (7) | −0.0004 (6) | 0.0014 (5) | 0.0014 (6) |
C3 | 0.0219 (7) | 0.0284 (8) | 0.0166 (7) | −0.0022 (6) | 0.0045 (6) | −0.0036 (6) |
C4 | 0.0207 (7) | 0.0228 (8) | 0.0229 (7) | −0.0010 (6) | 0.0085 (6) | 0.0005 (6) |
C5 | 0.0190 (7) | 0.0285 (9) | 0.0219 (7) | 0.0036 (6) | −0.0002 (6) | 0.0010 (6) |
C6 | 0.0201 (7) | 0.0268 (8) | 0.0182 (7) | 0.0006 (6) | 0.0002 (6) | −0.0019 (6) |
C7 | 0.0242 (8) | 0.0250 (8) | 0.0257 (8) | 0.0009 (6) | 0.0078 (6) | −0.0015 (6) |
C8 | 0.0211 (7) | 0.0204 (8) | 0.0216 (7) | 0.0043 (6) | 0.0042 (6) | 0.0003 (6) |
C9 | 0.0183 (7) | 0.0198 (7) | 0.0161 (7) | −0.0006 (6) | 0.0032 (5) | 0.0016 (6) |
C10 | 0.0193 (7) | 0.0182 (7) | 0.0166 (7) | −0.0001 (6) | 0.0034 (5) | 0.0012 (5) |
C11 | 0.0238 (8) | 0.0219 (8) | 0.0166 (7) | 0.0007 (6) | 0.0024 (6) | 0.0002 (6) |
C12 | 0.0242 (7) | 0.0216 (8) | 0.0161 (7) | 0.0021 (6) | 0.0009 (6) | −0.0008 (6) |
C13 | 0.0206 (7) | 0.0270 (8) | 0.0185 (7) | 0.0018 (6) | −0.0001 (6) | 0.0003 (6) |
C14 | 0.0208 (7) | 0.0237 (8) | 0.0153 (7) | 0.0013 (6) | 0.0031 (5) | 0.0008 (6) |
C15 | 0.0211 (7) | 0.0254 (8) | 0.0212 (7) | 0.0060 (6) | 0.0015 (6) | 0.0032 (6) |
C16 | 0.0332 (9) | 0.0292 (9) | 0.0261 (8) | 0.0125 (7) | 0.0056 (7) | −0.0037 (7) |
C17 | 0.0347 (9) | 0.0293 (9) | 0.0193 (7) | 0.0091 (7) | 0.0018 (6) | −0.0046 (6) |
C18 | 0.0340 (9) | 0.0289 (9) | 0.0375 (9) | −0.0039 (8) | −0.0057 (7) | −0.0019 (7) |
C19 | 0.0365 (9) | 0.0412 (10) | 0.0205 (8) | 0.0113 (8) | 0.0064 (7) | 0.0078 (7) |
C20 | 0.0274 (9) | 0.0439 (11) | 0.0387 (10) | 0.0177 (8) | 0.0084 (7) | 0.0050 (8) |
C21 | 0.0221 (8) | 0.0189 (7) | 0.0229 (7) | 0.0044 (6) | 0.0045 (6) | −0.0022 (6) |
C22 | 0.0169 (7) | 0.0304 (9) | 0.0207 (7) | 0.0018 (6) | 0.0048 (6) | 0.0058 (6) |
C23 | 0.0310 (9) | 0.0233 (8) | 0.0313 (8) | 0.0007 (7) | 0.0059 (7) | 0.0023 (7) |
C24 | 0.0335 (9) | 0.0319 (9) | 0.0333 (9) | 0.0044 (7) | 0.0074 (7) | 0.0139 (7) |
C25 | 0.0330 (9) | 0.0425 (10) | 0.0210 (8) | 0.0055 (8) | 0.0044 (6) | 0.0052 (7) |
C26 | 0.0348 (9) | 0.0357 (10) | 0.0246 (8) | 0.0082 (8) | 0.0101 (7) | 0.0001 (7) |
C27 | 0.0264 (8) | 0.0242 (8) | 0.0251 (8) | 0.0061 (6) | 0.0078 (6) | 0.0040 (6) |
S1—O2 | 1.4293 (10) | C11—C12 | 1.5146 (19) |
S1—O1 | 1.4357 (10) | C12—C13 | 1.517 (2) |
S1—N1 | 1.6413 (14) | C12—C19 | 1.540 (2) |
S1—C1 | 1.7588 (15) | C12—C18 | 1.541 (2) |
O3—C21 | 1.2234 (18) | C14—C15 | 1.380 (2) |
O4—C9 | 1.2213 (17) | C14—H14 | 0.9500 |
O5—C13 | 1.2184 (18) | C15—C16 | 1.393 (2) |
O6—C15 | 1.3692 (17) | C16—C17 | 1.386 (2) |
O6—C20 | 1.4305 (19) | C16—H16 | 0.9500 |
N1—C21 | 1.4233 (19) | C17—H17 | 0.9500 |
N1—H1N | 0.856 (14) | C18—H18A | 0.9800 |
N2—C21 | 1.3380 (19) | C18—H18B | 0.9800 |
N2—C22 | 1.4670 (18) | C18—H18C | 0.9800 |
N2—H2N | 0.872 (14) | C19—H19A | 0.9800 |
N3—C13 | 1.3871 (18) | C19—H19B | 0.9800 |
N3—C9 | 1.3968 (18) | C19—H19C | 0.9800 |
N3—C8 | 1.4759 (18) | C20—H20A | 0.9800 |
C1—C2 | 1.393 (2) | C20—H20B | 0.9800 |
C1—C6 | 1.3935 (19) | C20—H20C | 0.9800 |
C2—C3 | 1.387 (2) | C22—C27 | 1.522 (2) |
C2—H2 | 0.9500 | C22—C23 | 1.526 (2) |
C3—C4 | 1.393 (2) | C22—H22 | 1.0000 |
C3—H3 | 0.9500 | C23—C24 | 1.529 (2) |
C4—C5 | 1.396 (2) | C23—H23A | 0.9900 |
C4—C7 | 1.508 (2) | C23—H23B | 0.9900 |
C5—C6 | 1.382 (2) | C24—C25 | 1.517 (2) |
C5—H5 | 0.9500 | C24—H24A | 0.9900 |
C6—H6 | 0.9500 | C24—H24B | 0.9900 |
C7—C8 | 1.529 (2) | C25—C26 | 1.519 (2) |
C7—H7A | 0.9900 | C25—H25A | 0.9900 |
C7—H7B | 0.9900 | C25—H25B | 0.9900 |
C8—H8A | 0.9900 | C26—C27 | 1.526 (2) |
C8—H8B | 0.9900 | C26—H26A | 0.9900 |
C9—C10 | 1.476 (2) | C26—H26B | 0.9900 |
C10—C14 | 1.3916 (19) | C27—H27A | 0.9900 |
C10—C11 | 1.3963 (19) | C27—H27B | 0.9900 |
C11—C17 | 1.396 (2) | ||
O2—S1—O1 | 119.79 (6) | O6—C15—C14 | 116.12 (13) |
O2—S1—N1 | 105.48 (7) | O6—C15—C16 | 124.05 (14) |
O1—S1—N1 | 107.90 (7) | C14—C15—C16 | 119.82 (13) |
O2—S1—C1 | 109.21 (7) | C17—C16—C15 | 119.79 (14) |
O1—S1—C1 | 108.07 (7) | C17—C16—H16 | 120.1 |
N1—S1—C1 | 105.49 (7) | C15—C16—H16 | 120.1 |
C15—O6—C20 | 116.95 (12) | C16—C17—C11 | 121.52 (14) |
C21—N1—S1 | 126.46 (10) | C16—C17—H17 | 119.2 |
C21—N1—H1N | 115.9 (13) | C11—C17—H17 | 119.2 |
S1—N1—H1N | 107.8 (13) | C12—C18—H18A | 109.5 |
C21—N2—C22 | 123.02 (13) | C12—C18—H18B | 109.5 |
C21—N2—H2N | 118.8 (11) | H18A—C18—H18B | 109.5 |
C22—N2—H2N | 118.1 (11) | C12—C18—H18C | 109.5 |
C13—N3—C9 | 124.75 (12) | H18A—C18—H18C | 109.5 |
C13—N3—C8 | 117.64 (11) | H18B—C18—H18C | 109.5 |
C9—N3—C8 | 117.60 (11) | C12—C19—H19A | 109.5 |
C2—C1—C6 | 120.89 (14) | C12—C19—H19B | 109.5 |
C2—C1—S1 | 119.59 (11) | H19A—C19—H19B | 109.5 |
C6—C1—S1 | 119.48 (11) | C12—C19—H19C | 109.5 |
C3—C2—C1 | 119.12 (13) | H19A—C19—H19C | 109.5 |
C3—C2—H2 | 120.4 | H19B—C19—H19C | 109.5 |
C1—C2—H2 | 120.4 | O6—C20—H20A | 109.5 |
C2—C3—C4 | 120.90 (13) | O6—C20—H20B | 109.5 |
C2—C3—H3 | 119.6 | H20A—C20—H20B | 109.5 |
C4—C3—H3 | 119.6 | O6—C20—H20C | 109.5 |
C3—C4—C5 | 118.90 (14) | H20A—C20—H20C | 109.5 |
C3—C4—C7 | 120.55 (13) | H20B—C20—H20C | 109.5 |
C5—C4—C7 | 120.47 (13) | O3—C21—N2 | 125.76 (14) |
C6—C5—C4 | 121.11 (13) | O3—C21—N1 | 118.35 (13) |
C6—C5—H5 | 119.4 | N2—C21—N1 | 115.88 (13) |
C4—C5—H5 | 119.4 | N2—C22—C27 | 109.13 (12) |
C5—C6—C1 | 119.07 (13) | N2—C22—C23 | 112.08 (12) |
C5—C6—H6 | 120.5 | C27—C22—C23 | 111.03 (12) |
C1—C6—H6 | 120.5 | N2—C22—H22 | 108.2 |
C4—C7—C8 | 108.68 (12) | C27—C22—H22 | 108.2 |
C4—C7—H7A | 110.0 | C23—C22—H22 | 108.2 |
C8—C7—H7A | 110.0 | C22—C23—C24 | 110.18 (13) |
C4—C7—H7B | 110.0 | C22—C23—H23A | 109.6 |
C8—C7—H7B | 110.0 | C24—C23—H23A | 109.6 |
H7A—C7—H7B | 108.3 | C22—C23—H23B | 109.6 |
N3—C8—C7 | 112.30 (12) | C24—C23—H23B | 109.6 |
N3—C8—H8A | 109.1 | H23A—C23—H23B | 108.1 |
C7—C8—H8A | 109.1 | C25—C24—C23 | 111.60 (13) |
N3—C8—H8B | 109.1 | C25—C24—H24A | 109.3 |
C7—C8—H8B | 109.1 | C23—C24—H24A | 109.3 |
H8A—C8—H8B | 107.9 | C25—C24—H24B | 109.3 |
O4—C9—N3 | 119.59 (13) | C23—C24—H24B | 109.3 |
O4—C9—C10 | 122.97 (12) | H24A—C24—H24B | 108.0 |
N3—C9—C10 | 117.42 (12) | C24—C25—C26 | 110.91 (13) |
C14—C10—C11 | 121.46 (13) | C24—C25—H25A | 109.5 |
C14—C10—C9 | 117.34 (12) | C26—C25—H25A | 109.5 |
C11—C10—C9 | 121.18 (12) | C24—C25—H25B | 109.5 |
C17—C11—C10 | 117.50 (13) | C26—C25—H25B | 109.5 |
C17—C11—C12 | 120.60 (12) | H25A—C25—H25B | 108.0 |
C10—C11—C12 | 121.90 (13) | C25—C26—C27 | 110.78 (13) |
C11—C12—C13 | 113.74 (11) | C25—C26—H26A | 109.5 |
C11—C12—C19 | 110.43 (12) | C27—C26—H26A | 109.5 |
C13—C12—C19 | 106.57 (12) | C25—C26—H26B | 109.5 |
C11—C12—C18 | 110.13 (13) | C27—C26—H26B | 109.5 |
C13—C12—C18 | 106.03 (13) | H26A—C26—H26B | 108.1 |
C19—C12—C18 | 109.78 (13) | C22—C27—C26 | 112.00 (13) |
O5—C13—N3 | 118.75 (14) | C22—C27—H27A | 109.2 |
O5—C13—C12 | 120.60 (13) | C26—C27—H27A | 109.2 |
N3—C13—C12 | 120.63 (12) | C22—C27—H27B | 109.2 |
C15—C14—C10 | 119.86 (13) | C26—C27—H27B | 109.2 |
C15—C14—H14 | 120.1 | H27A—C27—H27B | 107.9 |
C10—C14—H14 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5i | 0.86 (1) | 2.03 (2) | 2.8702 (17) | 167 (2) |
N2—H2N···O1 | 0.87 (1) | 2.15 (2) | 2.8404 (17) | 136 (2) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C27H33N3O6S |
Mr | 527.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 19.1494 (4), 10.7253 (3), 13.8024 (2) |
β (°) | 106.691 (1) |
V (Å3) | 2715.34 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.40 × 0.40 × 0.10 |
Data collection | |
Diffractometer | Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.937, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28737, 5325, 4361 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.101, 1.03 |
No. of reflections | 5325 |
No. of parameters | 376 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.43 |
Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5i | 0.856 (14) | 2.029 (15) | 2.8702 (17) | 167.3 (19) |
N2—H2N···O1 | 0.872 (14) | 2.151 (16) | 2.8404 (17) | 135.6 (15) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Footnotes
‡Current address: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, England.
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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.
Gliquidone is an anti-diabetic drug in the sulfonylurea class. It is used in the treatment of diabetes mellitus type 2. The conformation of the sulfonyl urea fragment is in agreement with the SLU-1 geometry discussed in a recent theoretical study [Kasetti et al. (2010)]. The same conformation was previously found in polymorph I of glimepiride (Iwata et al., 1997).
In the sulfonyl urea part, the molecule displays an intramolecular N–H···O=S bond. The second NH group is N–H···O=C bonded to the imide part of a neighbouring molecule. As a result of this interaction, H-bonded chains are formed, which possess glide symmetry and propagate parallel to the c-axis.