(E)-N′-{7-Meth­oxy­spiro­[chromeno[4,3-d]thia­zole-4,1′-cyclo­hexa­n]-2-yl}-N,N-dimethyl­acetimidamide

Kapoor, K.; Gupta, V.K.; Kant, R.; Vyas, P.M.; Joshi, M.J.; Menpara, K.M.; Ladva, K.D.

doi:10.1107/S1600536811040359

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2855-o2856

doi:10.1107/S1600536811040359

Open

access

(E)-N′-{7-Methoxyspiro[chromeno[4,3-d]thiazole-4,1′-cyclohexan]-2-yl}-N,N-dimethylacetimidamide

Kamini Kapoor,^a Vivek K. Gupta,^a Rajni Kant,^a ^* Poorvesh M. Vyas,^b Mihir J. Joshi,^b Kalpesh M. Menpara ^c and Kartik D. Ladva ^c

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics, University of Jammu, Jammu Tawi 180 006, India, ^bPhysics Department, Saurashtra University, Rajkot 360 005, India, and ^cShri M. N. Virani Science College, Rajkot 360 005, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 19 September 2011; accepted 30 September 2011; online 5 October 2011)

In the chromenothiazole ring system of the title molecule, C₂₀H₂₅N₃O₂S, the pyran ring is in a half-chair conformation. The dihedral angle between the thiazole and benzene rings is 14.78 (6)°. The cyclohexane ring is in a chair conformation. The crystal structure is stabilized by weak intermolecular 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_r = 371.49
Monoclinic, P 2₁ /n
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 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.02
3482 reflections
291 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040359/lh5340sup1.cif

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

checkCIF report

Comment top

Heterocyclic compounds containing nitrogen and sulfur are used for medical purposes for the treatment of different kinds of fungal and bacterial infection along with treatment of e.g. gastric ulcers and cancer (Bishayee et al., 1997; Cruz et al., 1995; Chitamber & Wereley, 1997). Thiazoles exhibit a wide range of biological activities (Pawar et al., 2009). Schiff bases and acetamidine play an important role in many biological processes. They are of great importance for the preparation of various pharmaceuticals and are used in many other areas of chemistry as starting materials. Their facile synthesis and numerous biological activities contribute greatly to their Schiff bases and acetamidine popularity (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). Therefore, Schiff bases and acetamidine of amino thiazoles are expected to be biologically active. We report herein the X-ray crystallographic studies of a novel acetamidine base derived from substituted 8-methoxyspiro[chromeno[4,3-d] [1,3]thiazole-4,1-cyclohexan]-2-amine as a possible hybrid antimicrobial agent. In the title compound (Fig. 1), the methoxy substituent at the C7 atom forms the torsion angle of 178.4 (2) ° [(+) antiperiplanar conformation] with the atom set O10/C7/C8/C9. The benzopyran ring has a half-chair conformation with asymmetry parameter: ΔC2(C4—O5) = 4.49 (Duax et al., 1975). The cyclohexane ring has a chair conformation. The asymmetry parameters are: ΔCs(C4)=0.24; ΔC2(C4—C12)= 0.88. The dihedral angle between the best least squares planes through the thiazole and benzene rings is 14.75 (7)°. The stabilization of crystal packing (Fig. 2) is influenced by intermolecular C—H···N and C—H···O hydrogen bonding [C6—H61···N1 (symmetry code: x + 1/2, -y + 1/2, z - 1/2); C19—H19B···O5 (symmetry code: x - 1/2, -y + 1/2, z + 1/2)]. These interactions link the molecules into chains that run parallel to [-1 0 1].

Related literature top

For the biological activity of heterocyclic compounds containing nitrogen and sulfur, see: Bishayee et al. (1997); Cruz et al. (1995); Chitamber & Wereley (1997); Pawar et al. (2009); 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 top

An ice cold solution of phosphorus oxychloride (0.85 mmol) in dry toluene(20 ml) was added to the suitable amount of acetamide (0.47 mmol), and the mixture was stirred for 30 min at room temperature. At the end of the reaction, 7-methoxyspiro[4,3-d][1,3]thiazole-4,1-cyclohexan]-2-amine (0.42 mmol) dissolved in dry toluene was added drop wise and the reaction mixture was refluxed for 6 h. The solution was then cooled, carefully poured into the ice-water, and made alkaline with 1 N NaOH solution. The organic layer was extracted with CHCl₃, washed to neutrality with water, dried over sodium sulfate, filtered and then evaporated in vacuo. The crude material was purified by column chromatography on silica gel eluting with a hexane/ethyl acetate(7:3) mixture. Single crystals suitable for X-ray measurements were obtained by crystallization from CHCl₃ at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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).

Figures top

	Fig. 1. The molecular sreucture with ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules. The broken lines show weak intermolecular hydrogen bonds.

(E)-N'-{7-Methoxyspiro[chromeno[4,3-d]thiazole- 4,1'-cyclohexan]-2-yl}-N,N-dimethylacetimidamide top

Crystal data top

C₂₀H₂₅N₃O₂S	F(000) = 792
M_r = 371.49	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3482 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −23→23
T_min = 0.892, T_max = 1.000	l = −12→12
56290 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)] = 0.043	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(F_o²) + (0.0521P)² + 0.884P] where P = (F_o² + 2F_c²)/3
3482 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₂₅N₃O₂S	V = 1987.78 (7) Å³
M_r = 371.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2510 (2) Å	µ = 0.18 mm⁻¹
b = 20.0273 (4) Å	T = 293 K
c = 10.7301 (2) Å	0.3 × 0.2 × 0.1 mm
β = 90.840 (2)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3482 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2835 reflections with I > 2σ(I)
T_min = 0.892, T_max = 1.000	R_int = 0.041
56290 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.18 e Å⁻³
3482 reflections	Δρ_min = −0.19 e Å⁻³
291 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅N₃O₂S
M_r	371.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.2510 (2), 20.0273 (4), 10.7301 (2)
β (°)	90.840 (2)
V (Å³)	1987.78 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.892, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	56290, 3482, 2835
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.02
No. of reflections	3482
No. of parameters	291
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2.

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to the UGC for research funding under research project F.No. 37–4154/2009 (J&K) (SR).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bishayee, A., Karmaker, R., Mandal, A., Kundu, S. N. & Chaterjee, M. (1997). Eur. J. Cancer Prev. 6, 58–70. CrossRef CAS PubMed Web of Science Google Scholar
Chitamber, C. R. & Wereley, J. P. (1997). J. Biol. Chem. 272, 12151–12157. PubMed Web of Science Google Scholar
Cruz, T. F., Morgon, A. & Min, W. (1995). Mol. Biochem. 153, 161–166. CrossRef CAS Web of Science Google Scholar
Dong, Y. B., Wang, L., Ma, J. P. & Zhao, X. X. (2006). Cryst. Growth Des. 6, 2475–2485. Web of Science CSD CrossRef CAS Google Scholar
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jayashree, B. S., Anuradha, D. & Venugopala, K. N. (2005). Asian J. Chem. 17, 2093–2097. CAS Google Scholar
Modi, J. D., Sabnis, S. S. & Deliwala, C. V. (1971). J. Med. Chem. 14, 450–451. CAS PubMed Web of Science Google Scholar
More, P. G., Bhalvankar, R. B. & Patter, S. C. (2001). J. Indian Chem. Soc. 78, 474–475. CAS Google Scholar
Murza, M. M., Kuvatov, Z. K. & Safarov, M. G. (1999). Chem. Heterocyl. Compd, 35, 1097–1103. CrossRef CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Pawar, M. J., Burungale, A. B. & Karale, B. K. (2009). Arkivoc, xiii, 97–107. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sutariya, B., Raziya, S. K., Mohan, S. & Rao, S. V. S. (2007). Indian J. Chem. Sect. B, 465, 884–887. Google Scholar
Vicini, P., Geronikaki, A., Incerti, M., Busonera, B. & Poni, G. (2003). Bioorg. Med. Chem. 11, 4785–4789. Web of Science CrossRef PubMed CAS Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2855-o2856

doi:10.1107/S1600536811040359

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-{7-Meth­­oxy­spiro­[chromeno[4,3-d]thia­zole-4,1′-cyclo­hexa­n]-2-yl}-N,N-di­methyl­acetimidamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-{7-Methoxyspiro[chromeno[4,3-d]thiazole-4,1′-cyclohexan]-2-yl}-N,N-dimethylacetimidamide