2-(Furan-2-yl)-5-(2-nitro-benz-yl)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

The title compound, C(20)H(16)N(2)O(4)S, was prepared by introduction of a 2-nitro-benzyl group to 2-(furan-2-yl)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one via an alkaline-catalysed reaction. The thia-zepine ring adopts a twist-boat conformation. The furan ring is oriented at dihedral angles of 56.75 (14) and 10.82 (14)° with respect to the two benzene rings, while the two benzene rings make a dihedral angle of 62.96 (10)°. Weak inter-molecular C-H⋯O hydrogen bonds occur in the crystal structure.

Related literature

The title compound was prepared as part of an investigation of novel GSK 3β inhibitors. For applications of non-ATP competitive glycogen synthase kinase 3β(GSK 3β) inhibitors, see: Martinez et al. (2002 ▶).

Experimental

Crystal data

C20H16N2O4S

M = 380.41

Monoclinic,

a = 11.061 (3) Å

b = 8.538 (3) Å

c = 19.340 (6) Å

β = 105.535 (4)°

V = 1759.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.18 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.971

7699 measured reflections

3458 independent reflections

2755 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.10

3458 reflections

244 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052098/xu5112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052098/xu5112Isup2.hkl

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

C20H16N2O4S	F(000) = 792
Mr = 380.41	Dx = 1.436 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1000 reflections
a = 11.061 (3) Å	θ = 2.6–26.7°
b = 8.538 (3) Å	µ = 0.21 mm−1
c = 19.340 (6) Å	T = 293 K
β = 105.535 (4)°	Block, light-yellow
V = 1759.7 (9) Å3	0.18 × 0.16 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3458 independent reflections
Radiation source: fine-focus sealed tube	2755 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.963, Tmax = 0.971	k = −9→10
7699 measured reflections	l = −23→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0823P)2 + 0.133P] where P = (Fo2 + 2Fc2)/3
3458 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.32 e Å−3
12 restraints	Δρmin = −0.34 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	0.88992 (5)	0.50517 (6)	0.22528 (3)	0.04348 (19)
N1	0.86748 (14)	0.47987 (17)	0.06247 (8)	0.0344 (4)
N2	0.54187 (16)	0.5826 (2)	−0.12646 (8)	0.0452 (4)
O1	1.1607 (2)	0.6320 (2)	0.34025 (9)	0.0879 (7)
O2	0.95960 (14)	0.70935 (17)	0.05012 (8)	0.0517 (4)
O3	0.62377 (17)	0.5009 (2)	−0.13854 (8)	0.0672 (5)
O4	0.44565 (16)	0.6131 (2)	−0.17221 (9)	0.0748 (5)
C1	1.2646 (3)	0.5769 (3)	0.38975 (14)	0.0791 (9)
H1A	1.2950	0.6160	0.4360	0.095*
C2	1.3141 (2)	0.4647 (4)	0.36370 (14)	0.0702 (7)
H2A	1.3846	0.4070	0.3869	0.084*
C3	1.2399 (3)	0.4454 (4)	0.29201 (15)	0.0882 (10)
H3A	1.2542	0.3736	0.2589	0.106*
C4	1.14695 (19)	0.5473 (2)	0.28057 (10)	0.0419 (5)
C5	1.04068 (17)	0.5900 (2)	0.21861 (10)	0.0394 (4)
H5A	1.0320	0.7042	0.2191	0.047*
C6	1.06808 (18)	0.5463 (2)	0.14781 (10)	0.0408 (5)
H6A	1.1432	0.6006	0.1442	0.049*
H6B	1.0844	0.4347	0.1476	0.049*
C7	0.96163 (17)	0.5866 (2)	0.08346 (10)	0.0383 (4)
C8	0.86766 (16)	0.3349 (2)	0.09979 (9)	0.0348 (4)
C9	0.87861 (17)	0.3321 (2)	0.17369 (10)	0.0393 (4)
C10	0.8751 (2)	0.1872 (3)	0.20661 (12)	0.0523 (5)
H10A	0.8841	0.1833	0.2558	0.063*
C11	0.8586 (2)	0.0509 (3)	0.16798 (13)	0.0585 (6)
H11A	0.8519	−0.0438	0.1904	0.070*
C12	0.8520 (2)	0.0544 (3)	0.09558 (13)	0.0513 (5)
H12A	0.8435	−0.0384	0.0695	0.062*
C13	0.85800 (18)	0.1954 (2)	0.06219 (11)	0.0417 (5)
H13A	0.8555	0.1970	0.0138	0.050*
C14	0.77070 (18)	0.5078 (2)	−0.00482 (10)	0.0371 (4)
H14A	0.7365	0.4077	−0.0245	0.045*
H14B	0.8098	0.5556	−0.0389	0.045*
C15	0.66344 (16)	0.6118 (2)	0.00252 (9)	0.0339 (4)
C16	0.55868 (17)	0.6482 (2)	−0.05424 (9)	0.0368 (4)
C17	0.46416 (19)	0.7472 (2)	−0.04634 (11)	0.0452 (5)
H17A	0.3964	0.7693	−0.0854	0.054*
C18	0.4709 (2)	0.8125 (2)	0.01949 (12)	0.0494 (5)
H18A	0.4080	0.8794	0.0253	0.059*
C19	0.5712 (2)	0.7785 (2)	0.07652 (11)	0.0473 (5)
H19A	0.5761	0.8220	0.1213	0.057*
C20	0.66531 (18)	0.6798 (2)	0.06802 (10)	0.0407 (4)
H20A	0.7323	0.6583	0.1076	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0388 (3)	0.0601 (4)	0.0317 (3)	0.0035 (2)	0.0097 (2)	−0.0043 (2)
N1	0.0350 (8)	0.0381 (8)	0.0275 (8)	0.0007 (6)	0.0037 (6)	0.0011 (6)
N2	0.0454 (9)	0.0529 (11)	0.0315 (9)	−0.0075 (8)	0.0002 (7)	0.0006 (7)
O1	0.1060 (14)	0.0885 (13)	0.0440 (9)	0.0542 (11)	−0.0236 (9)	−0.0251 (9)
O2	0.0547 (9)	0.0492 (8)	0.0477 (8)	−0.0111 (7)	0.0076 (7)	0.0070 (7)
O3	0.0678 (11)	0.0909 (13)	0.0368 (9)	0.0228 (9)	0.0033 (8)	−0.0118 (8)
O4	0.0579 (10)	0.1064 (15)	0.0429 (9)	0.0081 (10)	−0.0167 (7)	−0.0144 (9)
C1	0.0895 (19)	0.0787 (18)	0.0430 (13)	0.0247 (16)	−0.0275 (13)	−0.0115 (13)
C2	0.0528 (14)	0.0937 (19)	0.0517 (15)	0.0275 (13)	−0.0073 (11)	−0.0008 (14)
C3	0.0848 (19)	0.110 (2)	0.0542 (15)	0.0532 (18)	−0.0095 (14)	−0.0240 (15)
C4	0.0414 (10)	0.0460 (11)	0.0341 (10)	0.0044 (9)	0.0030 (8)	−0.0063 (8)
C5	0.0375 (10)	0.0409 (10)	0.0371 (10)	0.0039 (8)	0.0053 (8)	−0.0030 (8)
C6	0.0344 (9)	0.0517 (12)	0.0361 (10)	−0.0022 (8)	0.0089 (8)	−0.0026 (9)
C7	0.0385 (10)	0.0431 (11)	0.0343 (10)	−0.0003 (8)	0.0117 (8)	−0.0009 (8)
C8	0.0308 (9)	0.0395 (10)	0.0319 (9)	0.0018 (7)	0.0046 (7)	0.0029 (7)
C9	0.0346 (9)	0.0489 (11)	0.0327 (10)	0.0020 (8)	0.0063 (8)	0.0032 (8)
C10	0.0580 (13)	0.0588 (14)	0.0378 (11)	−0.0007 (11)	0.0092 (10)	0.0130 (10)
C11	0.0672 (15)	0.0487 (13)	0.0548 (14)	0.0000 (11)	0.0081 (12)	0.0148 (11)
C12	0.0561 (13)	0.0403 (11)	0.0521 (13)	0.0026 (10)	0.0051 (10)	0.0026 (9)
C13	0.0421 (10)	0.0447 (11)	0.0364 (10)	0.0030 (8)	0.0073 (8)	0.0008 (8)
C14	0.0409 (10)	0.0398 (10)	0.0283 (9)	0.0005 (8)	0.0051 (8)	−0.0004 (7)
C15	0.0367 (9)	0.0328 (9)	0.0313 (9)	−0.0058 (7)	0.0076 (7)	0.0035 (7)
C16	0.0381 (10)	0.0376 (10)	0.0326 (9)	−0.0074 (8)	0.0058 (8)	0.0015 (7)
C17	0.0363 (10)	0.0487 (12)	0.0455 (12)	0.0000 (9)	0.0023 (9)	0.0044 (9)
C18	0.0438 (11)	0.0492 (12)	0.0552 (13)	0.0075 (9)	0.0131 (10)	−0.0008 (10)
C19	0.0511 (12)	0.0504 (12)	0.0401 (11)	0.0016 (9)	0.0119 (9)	−0.0048 (9)
C20	0.0422 (10)	0.0443 (11)	0.0327 (10)	0.0019 (8)	0.0047 (8)	−0.0008 (8)

S1—C9	1.769 (2)	C8—C13	1.384 (3)
S1—C5	1.854 (2)	C8—C9	1.402 (3)
N1—C7	1.361 (2)	C9—C10	1.396 (3)
N1—C8	1.433 (2)	C10—C11	1.369 (3)
N1—C14	1.466 (2)	C10—H10A	0.9300
N2—O3	1.215 (2)	C11—C12	1.383 (3)
N2—O4	1.216 (2)	C11—H11A	0.9300
N2—C16	1.470 (2)	C12—C13	1.376 (3)
O1—C4	1.336 (3)	C12—H12A	0.9300
O1—C1	1.368 (3)	C13—H13A	0.9300
O2—C7	1.228 (2)	C14—C15	1.518 (3)
C1—C2	1.272 (4)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.419 (4)	C15—C20	1.389 (3)
C2—H2A	0.9300	C15—C16	1.401 (2)
C3—C4	1.319 (3)	C16—C17	1.384 (3)
C3—H3A	0.9300	C17—C18	1.374 (3)
C4—C5	1.482 (3)	C17—H17A	0.9300
C5—C6	1.526 (3)	C18—C19	1.370 (3)
C5—H5A	0.9800	C18—H18A	0.9300
C6—C7	1.506 (3)	C19—C20	1.382 (3)
C6—H6A	0.9700	C19—H19A	0.9300
C6—H6B	0.9700	C20—H20A	0.9300
C9—S1—C5	102.48 (9)	C10—C9—S1	119.28 (15)
C7—N1—C8	122.04 (15)	C8—C9—S1	122.32 (15)
C7—N1—C14	118.29 (15)	C11—C10—C9	121.33 (19)
C8—N1—C14	119.33 (14)	C11—C10—H10A	119.3
O3—N2—O4	122.38 (17)	C9—C10—H10A	119.3
O3—N2—C16	119.38 (16)	C10—C11—C12	119.9 (2)
O4—N2—C16	118.24 (18)	C10—C11—H11A	120.1
C4—O1—C1	107.33 (19)	C12—C11—H11A	120.1
C2—C1—O1	110.6 (2)	C13—C12—C11	119.8 (2)
C2—C1—H1A	124.7	C13—C12—H12A	120.1
O1—C1—H1A	124.7	C11—C12—H12A	120.1
C1—C2—C3	106.1 (2)	C12—C13—C8	120.85 (19)
C1—C2—H2A	127.0	C12—C13—H13A	119.6
C3—C2—H2A	127.0	C8—C13—H13A	119.6
C4—C3—C2	107.9 (2)	N1—C14—C15	114.53 (15)
C4—C3—H3A	126.0	N1—C14—H14A	108.6
C2—C3—H3A	126.0	C15—C14—H14A	108.6
C3—C4—O1	108.01 (19)	N1—C14—H14B	108.6
C3—C4—C5	135.4 (2)	C15—C14—H14B	108.6
O1—C4—C5	116.57 (17)	H14A—C14—H14B	107.6
C4—C5—C6	111.12 (15)	C20—C15—C16	115.38 (17)
C4—C5—S1	112.40 (14)	C20—C15—C14	120.58 (16)
C6—C5—S1	111.43 (13)	C16—C15—C14	124.03 (16)
C4—C5—H5A	107.2	C17—C16—C15	122.67 (17)
C6—C5—H5A	107.2	C17—C16—N2	115.49 (17)
S1—C5—H5A	107.2	C15—C16—N2	121.83 (17)
C7—C6—C5	112.73 (15)	C18—C17—C16	119.67 (18)
C7—C6—H6A	109.0	C18—C17—H17A	120.2
C5—C6—H6A	109.0	C16—C17—H17A	120.2
C7—C6—H6B	109.0	C19—C18—C17	119.42 (19)
C5—C6—H6B	109.0	C19—C18—H18A	120.3
H6A—C6—H6B	107.8	C17—C18—H18A	120.3
O2—C7—N1	120.66 (17)	C18—C19—C20	120.44 (19)
O2—C7—C6	121.97 (17)	C18—C19—H19A	119.8
N1—C7—C6	117.35 (17)	C20—C19—H19A	119.8
C13—C8—C9	119.62 (17)	C19—C20—C15	122.40 (18)
C13—C8—N1	119.29 (16)	C19—C20—H20A	118.8
C9—C8—N1	121.09 (16)	C15—C20—H20A	118.8
C10—C9—C8	118.34 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.49	3.401 (3)	168
C12—H12A···O2ii	0.93	2.59	3.381 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.49	3.401 (3)	168
C12—H12A⋯O2ii	0.93	2.59	3.381 (3)	144

Symmetry codes: (i) ; (ii) .