Gliquidone.

The title compound {systematic name: N-cyclo-hexyl-carba-moyl-4-[2-(7-meth-oxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetra-hydro-isoquinolin-2-yl)eth-yl]benzene-sulfonamide}, C(27)H(33)N(3)O(6)S, displays an intra-molecular N-H⋯O=S inter-action, as well as inter-molecular N-H⋯O=C hydrogen bonds. The latter inter-actions lead to the formation of hydrogen-bonded chains parallel to the c axis. The conformation of the sulfonyl-urea 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 = 527.62

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.03

5325 reflections

376 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.43 e Å−3

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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811016680/jh2285Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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)

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) .