(E)-N'-{7-Meth-oxy-spiro-[chromeno[4,3-d]thia-zole-4,1'-cyclo-hexa-n]-2-yl}-N,N-dimethyl-acetimidamide.

In the chromenothia-zole ring system of the title mol-ecule, C(20)H(25)N(3)O(2)S, the pyran ring is in a half-chair conformation. The dihedral angle between the thia-zole and benzene rings is 14.78 (6)°. The cyclo-hexane ring is in a chair conformation. The crystal structure is stabilized by weak inter-molecular C-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For the biological activity of heterocyclic compounds containing nitro­gen and sulfur, see: Bishayee et al. (1997 ▶); Cruz et al. (1995 ▶); Chitamber & Wereley (1997 ▶). For the biological activity of thiazoles, see: Pawar et al. (2009 ▶). Schiff bases and acetamidine play an important role in many biological processes and are of great importance for the preparation of various pharmaceuticals, see: More et al. (2001 ▶); Sutariya et al. (2007 ▶); Murza et al. (1999 ▶); Dong et al. (2006 ▶); Jayashree et al. (2005 ▶); Modi et al. (1971 ▶); Vicini et al. (2003 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C20H25N3O2S

M = 371.49

Monoclinic,

a = 9.2510 (2) Å

b = 20.0273 (4) Å

c = 10.7301 (2) Å

β = 90.840 (2)°

V = 1987.78 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.892, T max = 1.000

56290 measured reflections

3482 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.02

3482 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040359/lh5340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040359/lh5340Isup2.hkl

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

C20H25N3O2S	F(000) = 792
Mr = 371.49	Dx = 1.241 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24440 reflections
a = 9.2510 (2) Å	θ = 3.5–29.0°
b = 20.0273 (4) Å	µ = 0.18 mm−1
c = 10.7301 (2) Å	T = 293 K
β = 90.840 (2)°	Plate, light-brown
V = 1987.78 (7) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3482 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −23→23
Tmin = 0.892, Tmax = 1.000	l = −12→12
56290 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.884P] where P = (Fo2 + 2Fc2)/3
3482 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
N1	0.33437 (18)	0.18039 (8)	0.41748 (15)	0.0474 (4)
C2	0.2587 (2)	0.12626 (10)	0.39594 (19)	0.0467 (5)
C3A	0.4732 (2)	0.12918 (9)	0.26463 (18)	0.0428 (5)
S3	0.33236 (6)	0.07336 (3)	0.28200 (5)	0.05248 (19)
C4	0.6032 (2)	0.12315 (9)	0.18332 (17)	0.0410 (4)
O5	0.64694 (14)	0.19099 (6)	0.14928 (11)	0.0428 (3)
C5A	0.65071 (19)	0.23902 (8)	0.24074 (16)	0.0368 (4)
C6	0.7445 (2)	0.29214 (9)	0.22330 (18)	0.0395 (4)
C7	0.7481 (2)	0.34279 (9)	0.3113 (2)	0.0459 (5)
C8	0.6590 (3)	0.34051 (11)	0.4146 (2)	0.0551 (6)
C9	0.5632 (3)	0.28851 (11)	0.4276 (2)	0.0539 (5)
C9A	0.5568 (2)	0.23671 (9)	0.34111 (17)	0.0419 (4)
C9B	0.4543 (2)	0.18148 (9)	0.34258 (17)	0.0421 (4)
O10	0.83754 (17)	0.39732 (7)	0.30446 (15)	0.0619 (4)
C11	0.9325 (3)	0.40072 (13)	0.2026 (3)	0.0766 (8)
H11A	0.9927	0.3617	0.2020	0.115*
H11B	0.9919	0.4398	0.2104	0.115*
H11C	0.8772	0.4029	0.1262	0.115*
C12	0.5715 (3)	0.08891 (13)	0.0596 (2)	0.0562 (6)
C13	0.7053 (3)	0.08381 (14)	−0.0209 (3)	0.0693 (7)
C14	0.8293 (3)	0.05035 (14)	0.0475 (3)	0.0818 (9)
C15	0.8642 (3)	0.08530 (14)	0.1699 (3)	0.0693 (7)
C16	0.7304 (2)	0.08994 (12)	0.2511 (2)	0.0535 (5)
N17	0.13926 (19)	0.10532 (9)	0.45830 (17)	0.0537 (5)
C18	0.0370 (2)	0.14748 (11)	0.4842 (2)	0.0501 (5)
C19	0.0168 (3)	0.21331 (12)	0.4193 (2)	0.0657 (6)
H19A	0.0794	0.2155	0.3489	0.099*
H19B	0.0400	0.2489	0.4761	0.099*
H19C	−0.0818	0.2176	0.3915	0.099*
N20	−0.06057 (19)	0.12955 (11)	0.56983 (19)	0.0650 (5)
C21	−0.1802 (3)	0.17228 (18)	0.6067 (3)	0.0986 (11)
H21A	−0.1614	0.2174	0.5812	0.148*
H21B	−0.1900	0.1707	0.6956	0.148*
H21C	−0.2680	0.1569	0.5675	0.148*
C22	−0.0438 (4)	0.06674 (15)	0.6362 (3)	0.0923 (10)
H22A	−0.1023	0.0331	0.5963	0.139*
H22B	−0.0739	0.0723	0.7208	0.139*
H22C	0.0558	0.0533	0.6352	0.139*
H61	0.803 (2)	0.2918 (9)	0.1512 (18)	0.044 (5)*
H81	0.664 (2)	0.3751 (11)	0.477 (2)	0.058 (6)*
H91	0.499 (3)	0.2877 (11)	0.494 (2)	0.064 (7)*
H161	0.698 (2)	0.0457 (12)	0.275 (2)	0.061 (6)*
H162	0.752 (2)	0.1132 (11)	0.328 (2)	0.058 (6)*
H121	0.537 (2)	0.0441 (12)	0.079 (2)	0.061 (6)*
H122	0.493 (3)	0.1108 (13)	0.017 (2)	0.076 (8)*
H131	0.679 (3)	0.0603 (13)	−0.093 (3)	0.076 (8)*
H132	0.734 (3)	0.1291 (13)	−0.046 (2)	0.063 (7)*
H141	0.913 (3)	0.0497 (14)	−0.006 (3)	0.092 (9)*
H142	0.801 (3)	0.0054 (16)	0.064 (3)	0.093 (9)*
H151	0.942 (3)	0.0618 (14)	0.216 (3)	0.092 (9)*
H152	0.897 (3)	0.1321 (13)	0.153 (2)	0.068 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0512 (10)	0.0403 (9)	0.0512 (10)	−0.0060 (8)	0.0149 (8)	−0.0058 (7)
C2	0.0484 (11)	0.0394 (11)	0.0525 (12)	−0.0010 (9)	0.0098 (9)	−0.0008 (9)
C3A	0.0480 (11)	0.0324 (10)	0.0482 (11)	−0.0054 (8)	0.0072 (9)	−0.0044 (8)
S3	0.0512 (3)	0.0383 (3)	0.0684 (4)	−0.0089 (2)	0.0148 (3)	−0.0121 (2)
C4	0.0488 (11)	0.0285 (9)	0.0460 (11)	−0.0059 (8)	0.0086 (8)	−0.0056 (8)
O5	0.0580 (8)	0.0311 (7)	0.0395 (7)	−0.0040 (6)	0.0085 (6)	−0.0047 (5)
C5A	0.0429 (10)	0.0281 (9)	0.0393 (10)	0.0018 (7)	0.0003 (8)	−0.0033 (7)
C6	0.0408 (10)	0.0331 (10)	0.0446 (11)	0.0024 (8)	0.0035 (8)	0.0001 (8)
C7	0.0455 (11)	0.0329 (10)	0.0592 (12)	−0.0027 (8)	−0.0015 (9)	−0.0045 (9)
C8	0.0649 (14)	0.0389 (11)	0.0617 (13)	−0.0051 (10)	0.0081 (11)	−0.0193 (10)
C9	0.0628 (14)	0.0459 (12)	0.0534 (12)	−0.0069 (10)	0.0144 (11)	−0.0144 (10)
C9A	0.0479 (11)	0.0340 (10)	0.0438 (10)	−0.0021 (8)	0.0053 (8)	−0.0050 (8)
C9B	0.0475 (11)	0.0362 (10)	0.0428 (10)	−0.0028 (8)	0.0075 (8)	−0.0027 (8)
O10	0.0637 (10)	0.0431 (8)	0.0791 (11)	−0.0182 (7)	0.0083 (8)	−0.0145 (7)
C11	0.0684 (16)	0.0602 (15)	0.102 (2)	−0.0289 (13)	0.0216 (15)	−0.0149 (14)
C12	0.0602 (14)	0.0509 (14)	0.0579 (13)	−0.0119 (11)	0.0102 (11)	−0.0201 (11)
C13	0.0826 (18)	0.0614 (16)	0.0645 (16)	−0.0119 (14)	0.0242 (14)	−0.0268 (13)
C14	0.0795 (19)	0.0494 (15)	0.118 (3)	0.0057 (14)	0.0509 (19)	−0.0093 (15)
C15	0.0494 (14)	0.0596 (16)	0.099 (2)	0.0071 (12)	0.0135 (13)	0.0161 (15)
C16	0.0531 (13)	0.0411 (12)	0.0665 (15)	−0.0008 (10)	0.0051 (11)	0.0067 (11)
N17	0.0493 (10)	0.0446 (10)	0.0677 (11)	−0.0064 (8)	0.0177 (9)	−0.0025 (9)
C18	0.0402 (11)	0.0526 (12)	0.0575 (12)	−0.0095 (9)	0.0004 (9)	−0.0127 (10)
C19	0.0538 (13)	0.0627 (15)	0.0801 (16)	0.0048 (11)	−0.0125 (12)	−0.0052 (13)
N20	0.0440 (10)	0.0762 (14)	0.0753 (13)	−0.0106 (9)	0.0150 (9)	−0.0155 (11)
C21	0.0528 (16)	0.137 (3)	0.106 (2)	0.0069 (17)	0.0207 (15)	−0.033 (2)
C22	0.092 (2)	0.086 (2)	0.100 (2)	−0.0273 (17)	0.0405 (18)	0.0049 (17)

N1—C2	1.309 (3)	C12—H121	0.97 (2)
N1—C9B	1.380 (2)	C12—H122	0.96 (3)
C2—N17	1.366 (2)	C13—C14	1.510 (4)
C2—S3	1.762 (2)	C13—H131	0.94 (3)
C3A—C9B	1.353 (3)	C13—H132	0.98 (2)
C3A—C4	1.501 (3)	C14—C15	1.519 (4)
C3A—S3	1.7292 (19)	C14—H141	0.97 (3)
C4—O5	1.465 (2)	C14—H142	0.95 (3)
C4—C12	1.519 (3)	C15—C16	1.527 (3)
C4—C16	1.526 (3)	C15—H151	0.98 (3)
O5—C5A	1.374 (2)	C15—H152	1.00 (3)
C5A—C6	1.387 (3)	C16—H161	0.97 (2)
C5A—C9A	1.394 (3)	C16—H162	0.97 (2)
C6—C7	1.386 (3)	N17—C18	1.301 (3)
C6—H61	0.95 (2)	C18—N20	1.346 (3)
C7—O10	1.373 (2)	C18—C19	1.501 (3)
C7—C8	1.391 (3)	C19—H19A	0.9600
C8—C9	1.376 (3)	C19—H19B	0.9600
C8—H81	0.96 (2)	C19—H19C	0.9600
C9—C9A	1.393 (3)	N20—C22	1.452 (4)
C9—H91	0.94 (2)	N20—C21	1.458 (3)
C9A—C9B	1.457 (3)	C21—H21A	0.9600
O10—C11	1.414 (3)	C21—H21B	0.9600
C11—H11A	0.9600	C21—H21C	0.9600
C11—H11B	0.9600	C22—H22A	0.9600
C11—H11C	0.9600	C22—H22B	0.9600
C12—C13	1.523 (3)	C22—H22C	0.9600
C2—N1—C9B	110.04 (16)	C14—C13—C12	111.8 (2)
N1—C2—N17	127.00 (18)	C14—C13—H131	111.6 (16)
N1—C2—S3	114.16 (14)	C12—C13—H131	107.3 (16)
N17—C2—S3	118.62 (15)	C14—C13—H132	109.5 (14)
C9B—C3A—C4	122.24 (17)	C12—C13—H132	108.6 (14)
C9B—C3A—S3	109.23 (14)	H131—C13—H132	108 (2)
C4—C3A—S3	128.48 (14)	C13—C14—C15	111.5 (2)
C3A—S3—C2	89.18 (9)	C13—C14—H141	109.2 (17)
O5—C4—C3A	107.26 (14)	C15—C14—H141	110.7 (16)
O5—C4—C12	104.56 (16)	C13—C14—H142	107.4 (17)
C3A—C4—C12	113.46 (17)	C15—C14—H142	109.4 (18)
O5—C4—C16	108.01 (16)	H141—C14—H142	109 (2)
C3A—C4—C16	112.13 (17)	C14—C15—C16	110.9 (2)
C12—C4—C16	110.92 (18)	C14—C15—H151	110.9 (17)
C5A—O5—C4	118.37 (13)	C16—C15—H151	109.5 (17)
O5—C5A—C6	116.73 (16)	C14—C15—H152	109.6 (14)
O5—C5A—C9A	121.25 (16)	C16—C15—H152	107.3 (14)
C6—C5A—C9A	121.85 (16)	H151—C15—H152	109 (2)
C7—C6—C5A	118.55 (18)	C4—C16—C15	112.4 (2)
C7—C6—H61	123.5 (12)	C4—C16—H161	106.8 (13)
C5A—C6—H61	117.9 (12)	C15—C16—H161	110.5 (13)
O10—C7—C6	123.63 (18)	C4—C16—H162	110.4 (13)
O10—C7—C8	115.69 (17)	C15—C16—H162	110.8 (13)
C6—C7—C8	120.68 (18)	H161—C16—H162	105.7 (19)
C9—C8—C7	119.71 (19)	C18—N17—C2	120.09 (18)
C9—C8—H81	120.0 (13)	N17—C18—N20	118.0 (2)
C7—C8—H81	120.3 (13)	N17—C18—C19	123.8 (2)
C8—C9—C9A	121.1 (2)	N20—C18—C19	118.1 (2)
C8—C9—H91	120.6 (14)	C18—C19—H19A	109.5
C9A—C9—H91	118.2 (15)	C18—C19—H19B	109.5
C9—C9A—C5A	118.01 (18)	H19A—C19—H19B	109.5
C9—C9A—C9B	125.40 (18)	C18—C19—H19C	109.5
C5A—C9A—C9B	116.51 (16)	H19A—C19—H19C	109.5
C3A—C9B—N1	117.40 (17)	H19B—C19—H19C	109.5
C3A—C9B—C9A	119.39 (17)	C18—N20—C22	119.9 (2)
N1—C9B—C9A	123.18 (16)	C18—N20—C21	123.2 (2)
C7—O10—C11	117.49 (17)	C22—N20—C21	116.8 (2)
O10—C11—H11A	109.5	N20—C21—H21A	109.5
O10—C11—H11B	109.5	N20—C21—H21B	109.5
H11A—C11—H11B	109.5	H21A—C21—H21B	109.5
O10—C11—H11C	109.5	N20—C21—H21C	109.5
H11A—C11—H11C	109.5	H21A—C21—H21C	109.5
H11B—C11—H11C	109.5	H21B—C21—H21C	109.5
C4—C12—C13	112.2 (2)	N20—C22—H22A	109.5
C4—C12—H121	106.7 (13)	N20—C22—H22B	109.5
C13—C12—H121	109.2 (13)	H22A—C22—H22B	109.5
C4—C12—H122	110.2 (16)	N20—C22—H22C	109.5
C13—C12—H122	112.2 (16)	H22A—C22—H22C	109.5
H121—C12—H122	106 (2)	H22B—C22—H22C	109.5
C9B—N1—C2—N17	174.7 (2)	C4—C3A—C9B—N1	−176.95 (18)
C9B—N1—C2—S3	0.3 (2)	S3—C3A—C9B—N1	0.5 (2)
C9B—C3A—S3—C2	−0.26 (16)	C4—C3A—C9B—C9A	5.1 (3)
C4—C3A—S3—C2	176.97 (19)	S3—C3A—C9B—C9A	−177.50 (15)
N1—C2—S3—C3A	0.00 (17)	C2—N1—C9B—C3A	−0.5 (3)
N17—C2—S3—C3A	−174.98 (18)	C2—N1—C9B—C9A	177.41 (18)
C9B—C3A—C4—O5	−32.2 (3)	C9—C9A—C9B—C3A	−170.1 (2)
S3—C3A—C4—O5	150.85 (15)	C5A—C9A—C9B—C3A	13.4 (3)
C9B—C3A—C4—C12	−147.2 (2)	C9—C9A—C9B—N1	12.1 (3)
S3—C3A—C4—C12	35.9 (3)	C5A—C9A—C9B—N1	−164.47 (18)
C9B—C3A—C4—C16	86.2 (2)	C6—C7—O10—C11	−1.2 (3)
S3—C3A—C4—C16	−90.7 (2)	C8—C7—O10—C11	178.4 (2)
C3A—C4—O5—C5A	44.4 (2)	O5—C4—C12—C13	63.2 (3)
C12—C4—O5—C5A	165.17 (16)	C3A—C4—C12—C13	179.8 (2)
C16—C4—O5—C5A	−76.6 (2)	C16—C4—C12—C13	−53.0 (3)
C4—O5—C5A—C6	154.00 (16)	C4—C12—C13—C14	54.4 (3)
C4—O5—C5A—C9A	−30.6 (2)	C12—C13—C14—C15	−55.2 (3)
O5—C5A—C6—C7	177.88 (16)	C13—C14—C15—C16	55.1 (3)
C9A—C5A—C6—C7	2.6 (3)	O5—C4—C16—C15	−60.5 (2)
C5A—C6—C7—O10	179.29 (18)	C3A—C4—C16—C15	−178.52 (19)
C5A—C6—C7—C8	−0.3 (3)	C12—C4—C16—C15	53.5 (3)
O10—C7—C8—C9	178.4 (2)	C14—C15—C16—C4	−54.7 (3)
C6—C7—C8—C9	−2.0 (3)	N1—C2—N17—C18	45.0 (3)
C7—C8—C9—C9A	2.1 (4)	S3—C2—N17—C18	−140.69 (18)
C8—C9—C9A—C5A	0.1 (3)	C2—N17—C18—N20	−164.45 (19)
C8—C9—C9A—C9B	−176.4 (2)	C2—N17—C18—C19	18.9 (3)
O5—C5A—C9A—C9	−177.56 (18)	N17—C18—N20—C22	4.1 (3)
C6—C5A—C9A—C9	−2.4 (3)	C19—C18—N20—C22	−179.0 (2)
O5—C5A—C9A—C9B	−0.7 (3)	N17—C18—N20—C21	−179.9 (2)
C6—C5A—C9A—C9B	174.37 (17)	C19—C18—N20—C21	−3.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O5i	0.96	2.41	3.335 (3)	161
C6—H61···N1ii	0.95 (2)	2.59 (2)	3.441 (3)	149.3 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯O5i	0.96	2.41	3.335 (3)	161
C6—H61⋯N1ii	0.95 (2)	2.59 (2)	3.441 (3)	149.3 (15)

Symmetry codes: (i) ; (ii) .