Gliquidone

Gelbrich, T.; Haddow, M.F.; Griesser, U.J.

doi:10.1107/S1600536811016680

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1343

doi:10.1107/S1600536811016680

Open

access

Gliquidone

Thomas Gelbrich,^a ^* Mairi F. Haddow ^a ‡ and Ulrich J. Griesser ^a

^aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
^*Correspondence e-mail: thomas.gelbrich@uibk.ac.at

(Received 29 April 2011; accepted 3 May 2011; online 7 May 2011)

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

C₂₇H₃₃N₃O₆S
M_r = 527.62
Monoclinic, P 2₁ /c
a = 19.1494 (4) Å
b = 10.7253 (3) Å
c = 13.8024 (2) Å
β = 106.691 (1)°
V = 2715.34 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.937, T_max = 0.984
28737 measured reflections
5325 independent reflections
4361 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.03
5325 reflections
376 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016680/jh2285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016680/jh2285Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016680/jh2285Isup3.cml

checkCIF report

Comment top

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.

Related literature top

For theoretical studies, 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 top

The investigated sample of gliquidone was obtained from Boehriger Ingelheim.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary size.
	Fig. 2. Fragment of an N–H···O=C-bonded chain. The crystal structure is viewed along [100]. H and O atoms directly engaged in H-bonds are drawn as balls.

N-cyclohexylcarbamoyl-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4- tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide top

Crystal data top

C₂₇H₃₃N₃O₆S	F(000) = 1120
M_r = 527.62	D_x = 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

Data collection top

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	R_int = 0.044
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ϕ and ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→13
T_min = 0.937, T_max = 0.984	l = −15→17
28737 measured reflections

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)] = 0.038	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(F_o²) + (0.054P)² + 0.7288P] where P = (F_o² + 2F_c²)/3
5325 reflections	(Δ/σ)_max = 0.001
376 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₇H₃₃N₃O₆S	V = 2715.34 (10) Å³
M_r = 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)°

Data collection top

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)
T_min = 0.937, T_max = 0.984	R_int = 0.044
28737 measured reflections

Refinement top

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	Δρ_max = 0.28 e Å⁻³
5325 reflections	Δρ_min = −0.43 e Å⁻³
376 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.937, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	28737, 5325, 4361
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

References

Endo, T., Iwata, M., Nagase, H., Shiro, M. & Ueda, H. (2003). STP Pharma Sci. 13, 281–286. CAS Google Scholar
Grell, W., Hurnaus, R., Griss, G., Sauter, R., Rupprecht, E., Mark, M., Luger, P., Nar, H., Wittneben, H. & Müller, P. (1998). J. Med. Chem. 41, 5219–5246. Web of Science CrossRef PubMed Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Iwata, M., Nagase, H., Endo, T. & Ueda, H. (1997). Acta Cryst. C53, 329–331. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kasetti, Y., Patel, N. K., Sundriyal, S. & Bharatam, P. V. (2010). J. Phys. Chem. B, 114, 11603–11610. Web of Science CrossRef CAS PubMed Google Scholar
Kobelt, D. & Paulus, E. F. (1972). Acta Cryst. B28, 3452–3457. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Kuhnert-Brandstätter, M., Geiler, M. & Wurian, I. (1982). Sci. Pharm. 50, 324–331. Google Scholar
Lins, L., Brasseur, R. & Malaisse, W. J. (1996). Pharm. Res. 34, 9–10. CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: AcademicPress. Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar